Isophthalaldehyde → 3-Vinylbenzaldehyde

HRID 22589

반응식

HRID 22589 반응식
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[CH:6](=O)[C:7]1C=CC=[C:9]([CH:10]=[O:11])[CH:8]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[CH:3]([C:2]1[CH:1]=[C:9]([CH:8]=[CH:7][CH:6]=1)[CH:10]=[O:11])=[CH2:4]

참가 물질

5

반응물 2

HCID 34777IsophthalaldehydeHCID 178418339Butyllithium

생성물 1

HCID 393903-Vinylbenzaldehyde

시약·촉매·용매 2

HCID 74505Methyltriphenyliphosphonium bromide촉매HCID 8028Tetrahydrofuran용매2회

실험 절차

To a suspension of methyltriphenylphosphonium bromide (27.2 g) in THF (200 mL) at 0° was added dropwise n-butyllithium (47 mL of 1.6M in hexane). The reaction mixture was stirred 30 min at 0° and cooled to -10°. The reaction mixture at -10° was transferred dropwise through a canula to a solution of isophthalaldehyde (10.0 g) in THF (300 mL) at -50°. The reaction was allowed to warm up to room temperature. After 3.5 hours at room temperature the reaction mixture was quenched with NH4OAc buffer (200 mL). The reaction mixture was extracted with ethyl acetate, dried over sodium sulfate and evaporated. Flash chromatography of the residue starting with 10% and finishing with 15% of diethyl ether in hexane afforded the title compound.

후처리

  1. temperaturecooled to -10°
  2. customat -10°
  3. customAfter 3.5 hours at room temperature the reaction mixture was quenched with NH4OAc buffer (200 mL)
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. customevaporated

출처 및 근거

ORD 기록
ord-338225b17c69438bb9afb8a932a6624b
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428171

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