Cyclohexene, 1-((trimethylsilyl)oxy)- → beta(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanol

HRID 376004

Reaction equation

HRID 376004 reaction equation
[CH2:1]([O:8][C@@H:9]([C@H:12]([OH:15])[CH2:13][OH:14])[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16]1(O[Si](C)(C)C)[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]=1>C(OCC)C.Cl>[CH2:1]([O:8][C@@H:9]([C@H:12]1[CH2:13][O:14][C:16]2([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[O:15]1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 81161Cyclohexene, 1-((trimethylsilyl)oxy)-HCID 10867592(2R,3R)-(-)-2-Benzyloxy-1,3,4-butanetriol

Product 1

HCID 53702433beta(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanolYield 96,624.102%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 3283Diethyl EtherSolvent

Procedure

4.34 g (0.02 mol) of (2R,3R)-2-benzyloxybutane-1,3,4-triol were suspended in a mixture of 3.4 g (0.02 mmol) of 1-cyclohexenyloxytrimethylsilane and 40 ml of diethyl ether. Two drops of concentrated hydrochloric acid were added and the mixture was stirred at room temperature for 30 minutes. The mixture was then evaporated to give 5.65 g of β(R)-benzyloxy-1,4-dioxaspiro[4,5]decane-2(R)-ethanol in the form of a colourless viscous oil; MS: m/e 292 [M]+.

Workup

  1. customThe mixture was then evaporated

Sources & evidence

ORD record
ord-b6b2329048bf4e38843d8e433579907f
Source dataset
uspto-grants-1996_01
Patent number
US05488115

Linked notes

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