Triethylamine → [5-(2-Benzyloxy-ethyl)-cyclohex-1-enylmethoxy]-tert-butyl-dimethyl-silane

HRID 910790Notes

Reaction equation

HRID 910790 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:16][C:15]([CH2:17][OH:18])=[CH:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:26][C:27]([Si:30](Cl)([CH3:32])[CH3:31])([CH3:29])[CH3:28]>CN(C=O)C>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]1[CH2:16][C:15]([CH2:17][O:18][Si:30]([C:27]([CH3:29])([CH3:28])[CH3:26])([CH3:32])[CH3:31])=[CH:14][CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 21879600{5-[2-(Benzyloxy)ethyl]cyclohex-1-en-1-yl}methanol

Product 1

HCID 21879598[5-(2-Benzyloxy-ethyl)-cyclohex-1-enylmethoxy]-tert-butyl-dimethyl-silaneYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate R3 was dissolved in THF (100 mL) and added to a solution of DIBAL (70 mL, 1M in hexanes) in THF (160 mL) at −35° C. for 35 minutes. The mixture was quenched with Rochelle's salt solution, and extracted with ether. The dried residue was purified by chromatography on SiO2 with 30% EtOAc:Hx to yield [5-(2-benzyloxy-ethyl)-cyclohex-1-enyl]-methanol 4.6 g (80%). A solution of the alcohol (4.0 g, 18.7 mmol) in DMF (60 mL) was treated with triethylamine (3 mL) followed by TBSCl (3.0 g, 22.4 mol) for 20 minutes at room temperature. The residue was isolated from an aqueous work-up and purified by chromatography to give [5-(2-benzyloxy-ethyl)-cyclohex-1-enylmethoxy]-tert-butyl-dimethyl-silane (Intermediate R4) 3.6 g (63%).

Workup

  1. customThe residue was isolated from an aqueous work-up
  2. custompurified by chromatography

Sources & evidence

ORD record
ord-4091888ca1f74080969602d017fad085
Source dataset
uspto-grants-2011_09
Patent number
US08022226B2

Reaction notes

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