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

HRID 133167Notes

Reaction equation

HRID 133167 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 A3 (6.5 g) was dissolved in THF (100 mL) and added to a solution of DIBAL (70 mL, 1M in hexanes) (available from Aldrich) in THF (160 mL) at −35° C. for 35 m. 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 m at rt. 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 A4) 3.6 g (63%).

Workup

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

Sources & evidence

ORD record
ord-42d804f4b7024545b7f03089cd754f3b
Source dataset
uspto-grants-2008_06
Patent number
US07390829B2

Reaction notes

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