2,2-Dimethoxypropane → 3-(4-Bromo-benzoyl)cyclohexanecarboxylic acid methyl ester

HRID 9563

반응식

HRID 9563 반응식
[Br:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([C@H:8]2[CH2:13][CH2:12][CH2:11][C@H:10]([C:14]([OH:16])=[O:15])[CH2:9]2)=[O:7])=[CH:4][CH:3]=1.[CH3:19]OC(OC)(C)C>CO.Cl.O1CCOCC1>[CH3:19][O:15][C:14]([CH:10]1[CH2:11][CH2:12][CH2:13][CH:8]([C:6](=[O:7])[C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:18][CH:17]=2)[CH2:9]1)=[O:16]

참가 물질

6

반응물 2

HCID 64952,2-DimethoxypropaneHCID 67147299trans-3-(4-Bromobenzoyl)cyclohexane-1-carboxylic acid

생성물 1

HCID 235493383-(4-Bromo-benzoyl)cyclohexanecarboxylic acid methyl ester수율 95.7%

시약·촉매·용매 3

HCID 313Hydrochloric Acid촉매HCID 887Methanol용매HCID 312751,4-Dioxane용매

반응 조건

온도
50 °C

실험 절차

To a solution of trans-3-(4-bromobenzoyl)cyclohexane-1-carboxylic acid (500 mg, 1.61 mmol, obtained from Rieke Metals Inc., Lincoln, Nebr., USA) and 2,2-dimethoxypropane (669 mg, 6.43 mmol) in methanol (20 mL), 5 drops of 4 M HCl in dioxane was added, and this reaction mixture was heated at 50° C. overnight. The solvent was removed by rotary evaporation to give the product 3-(4-bromo-benzoyl)-cyclohexanecarboxylic acid methyl ester as a brown oil (500 mg, yield 95.7%). 1H NMR (300 MHz, DMSO) δ 7.80 (d, 2 H), 7.60 (d, 2 H), 3.70 (s, 3 H), 3.25 (m, 1 H), 2.50 (m, 1 H), 2.20–1.90 (m, 4 H), 1.70–1.50 (m, 4 H); LC-MS ret. time 3.30 min, m/z 324.9 (MH+).

후처리

  1. customThe solvent was removed by rotary evaporation

출처 및 근거

ORD 기록
ord-91d88768cce04ee0ad43e92984f286b8
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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