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

HRID 351435

Reaction equation

HRID 351435 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-cccc71e19d034744869a56f0a372cf5c
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Linked notes

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