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

HRID 1721132Notes

Reaction equation

HRID 1721132 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-a6692d4262f346bbac26d1b979a0e504
Source dataset
uspto-grants-1996_04
Patent number
US05508430

Reaction notes

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