Methanol → HCID 9904585, compound

HRID 2301350Notes

Reaction equation

HRID 2301350 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[O:11][C:12]4[C:17]([C:18](=[O:21])[C:19]=3[OH:20])=[CH:16][C:15]([Cl:22])=[CH:14][CH:13]=4)=[CH:9][C:4]=2[O:3]C1.B(Br)(Br)Br.CO>C(Cl)Cl>[Cl:22][C:15]1[CH:16]=[C:17]2[C:12](=[CH:13][CH:14]=1)[O:11][C:10]([C:8]1[CH:7]=[CH:6][C:5]([OH:1])=[C:4]([OH:3])[CH:9]=1)=[C:19]([OH:20])[C:18]2=[O:21]

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 9818388HCID 9818388, compound

Product 1

HCID 9904585HCID 9904585, compoundYield 72,704,984%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 mg (31.6 pmol) of the compound obtained in Example 12 was dissolved in 2 ml of methylenechloride, 3 molar equivalents of boron tribromide (BBr3) was added thereto, and then the mixture was stirred at room temperature for 2 hours. The remained boron tribromide (BBr3) was decomposed with methanol. The residue was concentrated under reduced pressure, and purified by preparative TLC to give 7 mg of the title compound in a yield of 72%.

Workup

  1. concentrationThe residue was concentrated under reduced pressure
  2. custompurified by preparative TLC

Sources & evidence

ORD record
ord-afcd08e87adc49b1ab75b9f97826c04b
Source dataset
uspto-grants-2002_12
Patent number
US06500846B1

Reaction notes

Loading…