Methanol → HCID 15703788, compound

HRID 1534373Notes

Reaction equation

HRID 1534373 reaction equation
B(Br)(Br)Br.[CH3:5][CH:6]([CH3:32])[CH2:7][C:8]([C:10]1[CH:29]=[CH:28][C:13]2[O:14][C:15]3[C:24]([O:25][CH3:26])=[CH:23][C:22]([CH3:27])=[CH:21][C:16]=3[CH2:17][O:18][C:19](=[O:20])[C:12]=2[C:11]=1[O:30]C)=[O:9].CO>ClCCl>[OH:30][C:11]1[C:12]2[C:19](=[O:20])[O:18][CH2:17][C:16]3[CH:21]=[C:22]([CH3:27])[CH:23]=[C:24]([O:25][CH3:26])[C:15]=3[O:14][C:13]=2[CH:28]=[CH:29][C:10]=1[C:8](=[O:9])[CH2:7][CH:6]([CH3:5])[CH3:32]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 15703848HCID 15703848, compound

Product 1

HCID 15703788HCID 15703788, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

10.8 ml of a 1M boron tribromide solution in dichloromethane are added dropwise at -70° C. under argon to a solution of 6.2 g (16.1 mmol) of 3-(3-methyl-1-butanonyl)-4,11-dimethoxy-9-methyl-7H-dibenzo[b,g][1,5]-dioxocin-5-one in 160 ml of dichloromethane. After 1.5 h, 6 ml of methanol are added and the solution is brought to room temperature after a further 40 minutes. It is washed with sodium hydrogen carbonate solution and water, dried over magnesium sulphate and concentrated in vacuo. The residue is purified on a silica gel column using petroleum ether/ethyl acetate 6:1.

Workup

  1. waitthe solution is brought to room temperature after a further 40 minutes
  2. washIt is washed with sodium hydrogen carbonate solution and water
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified on a silica gel column

Sources & evidence

ORD record
ord-1c3d2502ba2e4f4890a6c3c271c6426b
Source dataset
uspto-grants-1992_02
Patent number
US05089487

Reaction notes

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