Sodium bis(trimethylsilyl)amide → 4-(4-Fluoro-3-methoxyphenyl)but-3-enoic acid

HRID 63637

반응식

HRID 63637 반응식
[Br-].[C:2]([CH2:5][CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:4])=[O:3].C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH:41]=O)=[CH:39][C:38]=1[O:45][CH3:46]>C1COCC1.O>[F:36][C:37]1[CH:44]=[CH:43][C:40]([CH:41]=[CH:6][CH2:5][C:2]([OH:4])=[O:3])=[CH:39][C:38]=1[O:45][CH3:46]

참가 물질

6

반응물 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 2733850(2-Carboxyethyl)triphenylphosphonium bromideHCID 27373584-Fluoro-3-methoxybenzaldehyde

생성물 1

HCID 1234648334-(4-Fluoro-3-methoxyphenyl)but-3-enoic acid수율 88%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of (2-carboxyethyl)triphenylphosphonium bromide (14.8 g, 35.7 mmol) in THF (40 mL) was added NaHMDS (35.8 mL, 71.5 mmol) at −20° C., and the reaction was stirred for 20 min. 4-Fluoro-3-methoxybenzaldehyde (5.0 g, 32.5 mmol) was added to the reaction at −78° C., and the reaction was stirred overnight while warming to rt. The reaction was diluted with water (30 mL) and extracted with EtOAc (3×30 mL). Organics were washed with brine (30 mL), dried (Na2SO4), and concentrated to give 6.0 g (88%) of the crude title compound as a yellow solid. [M+H] Calc'd for C11H11FO3, 211. Found, 211.

후처리

  1. stirringthe reaction was stirred overnight
  2. extractionextracted with EtOAc (3×30 mL)
  3. washOrganics were washed with brine (30 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d4b82c32f5b84eb5b871baa937977e4c
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447046B2

연결된 노트

불러오는 중…