2,3-Dimethylbenzaldehyde → (3E)-4-(2,3-dimethylphenyl)but-3-enoic acid

HRID 63091

반응식

HRID 63091 반응식
[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Br-].[C:22]([CH2:25][CH2:26][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:24])=[O:23]>C1COCC1.O>[CH3:1][C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1/[CH:4]=[CH:26]/[CH2:25][C:22]([OH:24])=[O:23]

참가 물질

6

반응물 3

HCID 342242,3-DimethylbenzaldehydeHCID 2724254Sodium bis(trimethylsilyl)amideHCID 2733850(2-Carboxyethyl)triphenylphosphonium bromide

생성물 1

HCID 86728217(3E)-4-(2,3-dimethylphenyl)but-3-enoic acid수율 99%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2,3-dimethylbenzaldehyde (17.0 g, 41.0 mmol) in THF (40 mL) was added NaHMDS (41.1 mL, 82.1 mmol) at −20° C., and the reaction was stirred for 20 min. (2-Carboxyethyl)triphenylphosphonium bromide (5.0 g, 37.3 mmol) was added to the reaction at −78° C., and reaction was stirred while warming to rt overnight. The solution was diluted with water (50 mL) and extracted with EtOAc (50×3 mL). Organics were washed with brine (50 mL), dried (Na2SO4), and concentrated to give 7.00 g (99%) of the crude title compound as a yellow solid. [M+H] calc'd for C12H14O2, 191; found 191.

후처리

  1. additionwas added to the reaction at −78° C.
  2. customreaction
  3. extractionextracted with EtOAc (50×3 mL)
  4. washOrganics were washed with brine (50 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b4c960a2086c4809b52c9f89eab5756b
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447045B2

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