Sodium Carbonate → 4-(7-Bromo-1,3-benzodioxol-4-yl)-4-methyl-2-oxo-valeric acid-ethyl ester

HRID 2055020노트

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HRID 2055020 반응식
[Br:1][C:2]1[C:7]2[O:8][CH2:9][O:10][C:6]=2[C:5]([C:11](O)([CH3:13])[CH3:12])=[CH:4][CH:3]=1.[CH2:15]([O:17][C:18](=[O:26])[C:19]([O:21][Si](C)(C)C)=[CH2:20])[CH3:16].[Sn+6].[Cl-].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:15]([O:17][C:18](=[O:26])[C:19](=[O:20])[CH2:21][C:11]([C:5]1[C:6]2[O:10][CH2:9][O:8][C:7]=2[C:2]([Br:1])=[CH:3][CH:4]=1)([CH3:13])[CH3:12])[CH3:16]

참가 물질

6

반응물 4

HCID 10340Sodium CarbonateHCID 111168062-Trimethylsilanyloxy-acrylic acid ethyl esterHCID 219488102-(7-Bromobenzo[1,3]dioxol-4-yl)-propan-2-olHCID 178479825HCID 178479825, 화합물

생성물 1

HCID 692037914-(7-Bromo-1,3-benzodioxol-4-yl)-4-methyl-2-oxo-valeric acid-ethyl ester수율 129.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-70 °C

실험 절차

1.77 g of 2-(7-bromobenzo[1,3]dioxol-4-yl)-propan-2-ol and 2.82 g of 2-trimethylsilyloxy-acrylic acid-ethyl ester (WO 00/32584) in 36 ml of dichloromethane are mixed at −70° C. with 1.10 ml of tin(VI)chloride. It is stirred for 20 minutes at −70° C. and then added to saturated sodium carbonate solution. It is extracted with dichloromethane, washed with water, dried and concentrated by evaporation in a vacuum. 3.15 g of 4-(7-bromo-1,3-benzodioxol-4-yl)-4-methyl-2-oxo-valeric acid-ethyl ester is obtained as a crude product. The latter is reacted for 4 hours at room temperature in 57 ml of a mixture that consists of 1N sodium hydroxide solution in ethanol/water. The batch is added to water, extracted with ether and then the aqueous phase is acidified with hydrochloric acid. It is extracted with ethyl acetate, washed with water, dried with sodium sulfate and concentrated by evaporation in a vacuum. 2.1 g of 4-(7-bromo-1,3-benzodioxol-4-yl)-4-methyl-2-oxo-valeric acid is obtained as a yellow oil.

후처리

  1. extractionIt is extracted with dichloromethane
  2. washwashed with water
  3. customdried
  4. concentrationconcentrated by evaporation in a vacuum

출처 및 근거

ORD 기록
ord-32e09eae21f64ec49d629e0aab969a98
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329753B2

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