Methanol → HCID 11610417, compound

HRID 554565Notes

Reaction equation

HRID 554565 reaction equation
B(Cl)(Cl)Cl.[CH3:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][C@H:21]2[C@H:26]([O:27]CC3C=CC=CC=3)[C@@H:25]([O:35]CC3C=CC=CC=3)[C@H:24]([O:43]CC3C=CC=CC=3)[C:23]([CH2:51][O:52]CC3C=CC=CC=3)=[CH:22]2)=[CH:9][CH:8]=1.CO>C(Cl)Cl>[OH:52][CH2:51][C:23]1[C@@H:24]([OH:43])[C@H:25]([OH:35])[C@@H:26]([OH:27])[C@H:21]([O:20][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][C:10]2[CH:9]=[CH:8][C:7]([O:6][CH3:5])=[CH:12][CH:11]=2)[CH:22]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25135Boron TrichlorideHCID 67459066HCID 67459066, compound

Product 1

HCID 11610417HCID 11610417, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a nitrogen stream, a boron trichloride 1.0 M methylene chloride solution (6.0 mL, 6.0 mmol) was added to a solution of 1-(4-methoxyphenyl)methyl-2-[(1R,4R,5S,6S)-4,5,6-trisbenzyloxy-3-(benzyloxymethyl)cyclohex-2-enyloxy]benzene (312 mg, 0.426 mmol) in methylene chloride (12 mL) at −78° C., and the mixture was stirred at the temperature for 1.5 hours. After addition of methanol, the temperature of the resulting solution was raised to room temperature and the solvent was distilled under reduced pressure. The obtained residue was purified by silica gel column chromatography [developing solution=methanol:methylene chloride (1:8)] to obtain the title compound (37.9 mg, 24%).

Workup

  1. distillationthe solvent was distilled under reduced pressure
  2. customThe obtained residue was purified by silica gel column chromatography [developing solution=methanol:methylene chloride (1:8)]

Sources & evidence

ORD record
ord-c363180b90fd439a88fb46d66d46d7b4
Source dataset
uspto-grants-2011_11
Patent number
US08048897B2

Reaction notes

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