• Name

  (Z)-4-[(Tetrahydro-2H-pyran-2-yl)oxy]-2-buten-1-ol

• EINECS
• CAS No. 57323-06-5
• Article Data28
• CAS DataBase
• Density 1.057g/cm³
• Solubility
• Melting Point
• Formula C9H16 O3
• Boiling Point 296.351°C at 760 mmHg
• Molecular Weight 172.224
• Flash Point 133.028°C
• Transport Information
• Appearance
• Safety
• Risk Codes
• Molecular Structure
• Hazard Symbols
• Synonyms 2-Buten-1-ol,4-[(tetrahydro-2H-pyran-2-yl)oxy]-, (Z)-;(Z)-4-[(Tetrahydropyranyl)oxy]-2-buten-1-ol; cis-2-Butene-1,4-diolmonotetrahydropyranyl ether
• PSA 38.69000
• LogP 1.07810

Synthetic route

64244-47-9

4-(tetrahydro-pyran-2-yloxy)-but-2-yn-1-ol

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

Conditions

Conditions	Yield
With hydrogen; Lindlar's catalyst In toluene	100%
With hydrogen; Pd-BaSO4 In methanol	77%
With dicobalt octacarbonyl; tri-n-butyl-tin hydride 2.) benzene, 65 deg C, 2 h; Yield given; Multistep reaction;

110-87-2

3,4-dihydro-2H-pyran

6117-80-2

1,4-butenediol

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

Conditions

Conditions	Yield
With Amberlyst 15 In tetrahydrofuran	93%
With tin(ll) chloride In chloroform for 24h; Ambient temperature;	75%
With pyridinium p-toluenesulfonate In tetrahydrofuran at 20℃; for 24h;	74%

222713-57-7

tert-butyl-dimethyl-[4-(tetrahydro-pyran-2-yloxy)-but-2-enyloxy]-silane

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

Conditions

Conditions	Yield
With zinc tetrafluoroborate In water for 5h; Ambient temperature;	89%
With oxone In methanol at 20℃; for 2.5h;	85%

110-87-2

3,4-dihydro-2H-pyran

6117-80-2

1,4-butenediol

A

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

B

72900-28-8

2-((Z)-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyloxy)-tetrahydro-2H-pyran

Conditions

Conditions	Yield
With Dowex 50W x 2 (50-100 mesh) In toluene at 30℃; for 0.166667h;	A 80% B 3%
toluene-4-sulfonic acid In ethyl acetate 1) 0 deg C, 40 min, 2) rt, 30 min;	A 53% B 15%
With toluene-4-sulfonic acid In tetrahydrofuran; dichloromethane at 0 - 20℃; Inert atmosphere;	A 46% B 24%

...Expand

110-87-2

3,4-dihydro-2H-pyran

821-11-4

(E)-2-butene-1,4-diol

24057-28-1

pyridinium p-toluenesulfonate

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

Conditions

Conditions	Yield
In tetrahydrofuran; dichloromethane	49%
In tetrahydrofuran; dichloromethane	49%
In tetrahydrofuran; dichloromethane	49%

...Expand

110-87-2

3,4-dihydro-2H-pyran

6117-80-2

1,4-butenediol

A

694-54-2

tetrahydro-2H-2-pyranol

B

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

C

72900-28-8

2-((Z)-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyloxy)-tetrahydro-2H-pyran

Conditions

Conditions	Yield
With Dowex 50W x 2 In toluene at 30℃; for 2.33333h; Etherification; hydration;	A n/a B 88 % Chromat. C 5 % Chromat.

...Expand

110-87-2

3,4-dihydro-2H-pyran

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1.1: 99 percent / p-TsOH / 0.75 h 2.1: n-BuLi / tetrahydrofuran 2.2: 92 percent / tetrahydrofuran / 1.25 h / ultasound irradiation 3.1: 100 percent / H2 / Lindlar's catalyst / toluene View Scheme

6089-04-9

3-(tetrahydropyran-2'-yloxy)propyne

trimethylene dihalide

trimethylene dihalide

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1.1: n-BuLi / tetrahydrofuran 1.2: 92 percent / tetrahydrofuran / 1.25 h / ultasound irradiation 2.1: 100 percent / H2 / Lindlar's catalyst / toluene View Scheme

110-87-2

3,4-dihydro-2H-pyran

821-11-4, 6117-80-2, 110-64-5

1,4-butenediol

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

Conditions

Conditions	Yield
With pyridinium p-toluenesulfonate In tetrahydrofuran at 0 - 20℃; for 21h;

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

41793-29-7

(Z)-4-chloro-1-<(tetrahydropyran-2-yl)oxy>but-2-ene

Conditions

Conditions	Yield
With 2,3,5-trimethyl-pyridine; methanesulfonyl chloride; lithium chloride In N,N-dimethyl-formamide 1.) 0 deg C; 2.) r.t.;	100%
With 2,4,6-trimethyl-pyridine; methanesulfonyl chloride; lithium chloride In N,N-dimethyl-formamide 0 deg C, 15 min then r.t., 1 h;	83%
With 2,3,5-trimethyl-pyridine; methanesulfonyl chloride; lithium chloride In N,N-dimethyl-formamide at 0 - 20℃;	83%

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

104226-67-7

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-enal

Conditions

Conditions	Yield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene In water; acetonitrile for 0.2h; pH 7;	95%
With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; 1,2-Dichloro-3-iodobenzene In chloroform at 50℃; for 1.5h;	77%
With manganese(IV) oxide In chloroform for 10h; Ambient temperature;	63%

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

(E)-4-(3,4,5,6-tetrahydropyran-2H-yloxy)but-2-en-1-al

Conditions

Conditions	Yield
With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; tetrakis(acetonitrile)copper(I) trifluoromethanesulfonate; 4,4'-Dimethoxy-2,2'-bipyridin; oxygen In acetonitrile at 20℃; for 5h; Schlenk technique; Inert atmosphere;	95%

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

5292-43-3

bromoacetic acid tert-butyl ester

475086-61-4

2-[4-(2-tetrahydropyranyloxy)-(Z)-2-buten-1-yloxy]acetic acid tert-butyl ester

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In water; toluene at 22℃; for 20h;	93%
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate In water; benzene at 0 - 20℃; for 1.16667h;

110-87-2

3,4-dihydro-2H-pyran

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

72900-28-8

2-((Z)-4-(tetrahydro-2H-pyran-2-yloxy)but-2-enyloxy)-tetrahydro-2H-pyran

Conditions

Conditions	Yield
With indium(III) chloride; 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate at 20℃; for 4h;	91%
With 1-butyl-3-methylimidazolium Tetrafluoroborate at 20℃; for 8h;	87%

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

17435-72-2

ethyl 2-bromomethyl-2-propenoate

1018388-08-3

(Z)-ethyl 2-{[4'-(tetrahydro-2''H-pyran-2''-yloxy)but-2'-enyloxy]methyl}acrylate

Conditions

Conditions	Yield
Stage #1: (2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: ethyl 2-bromomethyl-2-propenoate In tetrahydrofuran at 0 - 20℃; for 24h; Further stages.;	89%

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

2-chloro-4-(1-piperidinomethyl)-pyridine

146270-02-2

(Z)-4-(Piperidin-1-ylmethyl)-2-((4-((tetrahydro-2H-pyran2-yl)oxy)but-2-en-1-yl)oxy)pyridine

Conditions

Conditions	Yield
With tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate; sodium hydroxide In toluene for 15h; Reflux; Large scale;	88.2%
In tetrahydrofuran; chloroform; N,N-dimethyl-formamide	3.10 g (89%)

57323-06-5

(2Z)-4-(tetrahydropyran-2-yloxy)but-2-en-1-ol

2-Bromo-4-[1,3]dioxolan-2-yl-pyridine

118289-19-3

2-[4-(2-tetrahydropyranyloxy)-(Z)-2-buten-1-yloxy]-4-(1,3-dioxolan-2-yl)-pyridine

Conditions

Conditions	Yield
With sodium hydroxide; tetra(n-butyl)ammonium hydrogensulfate; potassium carbonate In toluene for 18h; Ambient temperature;	87%

(Z)-4-[(Tetrahydro-2H-pyran-2-yl)oxy]-2-buten-1-ol Chemical Properties

(Z)-4-[(Tetrahydro-2H-pyran-2-yl)oxy]-2-buten-1-ol Uses

(Z)-4-[(Tetrahydro-2H-pyran-2-yl)oxy]-2-buten-1-ol Safety Profile