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

HRID 63091

反応式

HRID 63091 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b4c960a2086c4809b52c9f89eab5756b
出典データセット
uspto-grants-2016_09
特許番号
US09447045B2

関連ノート

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