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

HRID 910790노트

반응식

HRID 910790 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-4091888ca1f74080969602d017fad085
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08022226B2

반응 노트

불러오는 중…