Methanol → HCID 56627644, compound

HRID 850915Notes

Reaction equation

HRID 850915 reaction equation
B(Br)(Br)Br.C1[O:27][C:26]2[CH:25]=[CH:24][C:9]([CH:10]=[C:11]3[CH2:20][CH2:19][C:18]4[C:13]([CH3:22])([CH2:14][CH2:15][C:16](=[O:21])[CH:17]=4)[C:12]3=[O:23])=[CH:8][C:7]=2[O:6]1.C(=O)([O-])[O-].[K+].[K+].CO>ClCCl.O>[OH:6][C:7]1[CH:8]=[C:9]([CH:24]=[CH:25][C:26]=1[OH:27])[CH:10]=[C:11]1[CH2:20][CH2:19][C:18]2[C:13]([CH3:22])([CH2:14][CH2:15][C:16](=[O:21])[CH:17]=2)[C:12]1=[O:23]

Participants

7

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 25134Boron tribromideHCID 57047156HCID 57047156, compound

Product 1

HCID 56627644HCID 56627644, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (0.28 ml, 0.003 mole) in dichloromethane (15.1) was added to a well stirred solution of 2-(3,4-methylenedioxybenzylidene)-3,4,8,8a-tetrahydro-8a-methyl-1,6(2H,7H)-naphthalenedione (9) (0.3 g, 0.001 mole) in dichloromethane (20 ml) containing potassium carbonate (1.0 g) at -78° C. under nitrogen. After 10 minutes the mixture was treated with methanol (1 ml) and poured into water. The organic phase was separated and dried (Na2SO4). The solvent was removed and the product was chromatographed on silica gel using ether as eluant. The title compound was obtained as a yellow crystalline solid (0.05 g, 17%) m.p. 193°-5° C.

Workup

  1. customThe organic phase was separated
  2. dry with materialdried (Na2SO4)
  3. customThe solvent was removed
  4. customthe product was chromatographed on silica gel

Sources & evidence

ORD record
ord-737e679c173a487a990334712dedca1d
Source dataset
uspto-grants-1983_05
Patent number
US04382094

Reaction notes

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