Hydrochloric Acid → Methyl trans-2-(4-bromobenzoyl)cyclobutanecarboxylate

HRID 9546

반응식

HRID 9546 반응식
[Br:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([C@@H:8]2[CH2:11][CH2:10][C@H:9]2[C:12]([OH:14])=[O:13])=[O:7])=[CH:4][CH:3]=1.[CH3:17]OC(OC)(C)C.Cl>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([C@@H:8]2[CH2:11][CH2:10][C@H:9]2[C:12]([O:14][CH3:17])=[O:13])=[O:7])=[CH:15][CH:16]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 64952,2-DimethoxypropaneHCID 58681302trans-2-(4-Bromobenzoyl)cyclobutanecarboxylic acid

생성물 1

HCID 58681309Methyl trans-2-(4-bromobenzoyl)cyclobutanecarboxylate수율 78%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of trans-2-(4-bromobenzoyl)cyclobutanecarboxylic acid (8.2 g, 28.94 mmol) in MeOH (250 mL) was added 2,2-dimethoxypropane (3.65 g, 35.02 mmol) and HCl (4.0 M in dioxane) (2.0 mL). The resulting solution was stirred at rt for 3 days, and then evaporated to dryness. The resulting residue was purified with flash chromatography (Biotage Flash 40M) using 4 to 11% ethyl acetate in hexanes to afford methyl trans-2-(4-bromobenzoyl)cyclobutanecarboxylate (6.21 g, 78%). 1H NMR (400 MHz, CD2Cl2) δ 2.14–2.39 (m, 4H), 3.62 (m, 1H), 3.68 (s, 3H), 4.24 (m, 1H), 7.63 (m, 2H), 7.80 (m, 2H).

후처리

  1. customevaporated to dryness
  2. customThe resulting residue was purified with flash chromatography (Biotage Flash 40M)

출처 및 근거

ORD 기록
ord-faa82ea8037f49a8beba89354950b23d
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091228B2

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