Boron trifluoride → 1-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde

HRID 351435

반응식

HRID 351435 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]([C:17]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)=[CH2:18])=[CH2:16])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:33][C:34](=[CH2:37])[CH:35]=[O:36].B(F)(F)F>C(Cl)Cl>[CH3:33][C:34]1([CH:35]=[O:36])[CH2:37][CH2:16][C:15]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][CH:11]=2)=[C:17]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[CH:23][CH:24]=2)[CH2:18]1

참가 물질

5

반응물 3

HCID 6356Boron trifluorideHCID 6562MethacroleinHCID 184363312,3-Di(4-benzyloxy-phenyl)-1,3-butadiene

생성물 1

HCID 865958461-Methyl-3,4-di(4-benzyloxy-phenyl)-cyclohex-3-ene carbaldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2,3-di(4-benzyloxy-phenyl)-1,3-butadiene (1.2 g, 2.8 mmol) and 2-methyl-propenal (0.602 g, 8.4 mmol) in DCM (10.5 mL) was added BF3.OCH2CH3 (0.596 mL, 4.2 mmol) at −10° C. After 3 h at −10° C., the reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL). The reaction mixture was then extracted with ethyl acetate (2 10 mL), dried over MgSO4 and purified by SiO2 twice (15% ethyl acetate/hexane) to yield 1-methyl-3,4-di(4-benzyloxy-phenyl )-cyclohex-3-ene carbaldehyde.

후처리

  1. customat −10° C
  2. customthe reaction mixture was quenched with saturated aqueous NaHCO3 (10 mL)
  3. extractionThe reaction mixture was then extracted with ethyl acetate (2 10 mL)
  4. dry with materialdried over MgSO4
  5. custompurified by SiO2 twice (15% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-cccc71e19d034744869a56f0a372cf5c
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183445B2

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