Boron trifluoride → 4-(4-Benzyloxy-phenyl)-1-methyl-cyclohex-3-ene carbaldehyde

HRID 351430

Reaction equation

HRID 351430 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[CH2:18])[CH:16]=[CH2:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20](=[CH2:23])[CH:21]=[O:22].B(F)(F)F>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[CH2:18][CH2:19][C:20]([CH3:23])([CH:21]=[O:22])[CH2:17][CH:16]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6356Boron trifluorideHCID 6562MethacroleinHCID 184363271-(Benzyloxy)-4-(buta-1,3-dien-2-yl)benzene

Product 1

HCID 865958454-(4-Benzyloxy-phenyl)-1-methyl-cyclohex-3-ene carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-benzyloxy-4-(1-methylene-allyl)-benzene (0.40 g, 1.694 mmol) and 2-methyl-propenal (0.355 mL) in DCM (10 mL) was cooled to −10° C. BF3.OCH2CH3 (0.322 mL, 1.778 mmol) was added and the reaction mixture stirred for 3 h. The mixture was then quenched by aqueous saturated NaHCO3 solution. After extraction with ethyl acetate (2×100 mL), the reaction mixture was dried over MgSO4 and purified on SiO2 to yield 4-(4-benzyloxy-phenyl)-1-methyl-cyclohex-3-ene carbaldehyde.

Workup

  1. additionOCH2CH3 (0.322 mL, 1.778 mmol) was added
  2. customThe mixture was then quenched by aqueous saturated NaHCO3 solution
  3. extractionAfter extraction with ethyl acetate (2×100 mL)
  4. dry with materialthe reaction mixture was dried over MgSO4
  5. custompurified on SiO2

Sources & evidence

ORD record
ord-04161045a5294dad8b51e523f70816bd
Source dataset
uspto-grants-2007_02
Patent number
US07183445B2

Linked notes

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