Acetic Anhydride → Acetic acid 1-(4-bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl ester

HRID 2180594노트

반응식

HRID 2180594 반응식
[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([CH:14]([OH:16])[CH3:15])[C:3]=1[O:17][CH3:18].Cl.CN(C)CCCN=C=NCC.[C:31](OC(=O)C)(=[O:33])[CH3:32]>CN(C)C1C=CN=CC=1.ClCCl>[Br:1][C:2]1[C:11]2[C:10]([CH3:13])([CH3:12])[CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([CH:14]([O:16][C:31](=[O:33])[CH3:32])[CH3:15])[C:3]=1[O:17][CH3:18]

참가 물질

6

반응물 3

HCID 7918Acetic AnhydrideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 224909511-(4-Bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol

생성물 1

HCID 69731470Acetic acid 1-(4-bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethyl ester

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1-(4-bromo-3-methoxy-5,5-dimethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-ethanol (Compound A-95, 12.3 g, 39 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI, 11.2 g, 58.5 mmol) and 4-dimethylaminopyridine (DMAP, 9.5 g, 78 mmol) in dichloromethane (350 mL) at room temperature was added acetic anhydride (3.7 mL, 39 mmol). After stirring at room temperature for 16 h, the mixture was quenched with water and extracted with diethyl ether. The combined ethereal layers were washed with water, brine, dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (silica gel, 5% ethyl acetate in hexane) to give the title compound as a colorless oil.

후처리

  1. customthe mixture was quenched with water
  2. extractionextracted with diethyl ether
  3. washThe combined ethereal layers were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography (silica gel, 5% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-58342e90bff94d1fa9a59737b2cbd834
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06887896B1

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