Methanol → HCID 53330279, compound

HRID 2042921Notes

Reaction equation

HRID 2042921 reaction equation
[Br:1][C:2]1[CH:20]=[C:19]([CH2:21][O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[C:18]([Cl:33])=[CH:17][C:3]=1[C:4](O[Si](C(C)C)(C(C)C)C(C)C)=[O:5].CSC.B.CO.O>C1COCC1>[Br:1][C:2]1[CH:20]=[C:19]([CH2:21][O:22][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:24]([CH3:25])[CH3:26])[CH:27]([CH3:28])[CH3:29])[C:18]([Cl:33])=[CH:17][C:3]=1[CH2:4][OH:5]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 12423031(Dimethyl sulfide)trihydroboronHCID 53330278HCID 53330278, compound

Product 1

HCID 53330279HCID 53330279, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of silyl ester 29 (38.0 g, 65.8 mmol) in THF (300 mL) was added borane dimethylsulfide complex (1 M in THF, 13 mL) at 0° C. The mixture was stirred 0° C. for 15 min, at room temperature at 30 min, and at 75° C. for 15 h. The mixture was cooled to 0° C. MeOH and H2O were added to the cooled mixture to quench the reaction. After dilution with water, the mixture was extracted with EtOAc. The organic layer was dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica column chromatography to provide the titled compound 30 (22.9 g, 85%).

Workup

  1. waitat 75° C. for 15 h
  2. temperatureThe mixture was cooled to 0° C
  3. customto quench
  4. customthe reaction
  5. extractionAfter dilution with water, the mixture was extracted with EtOAc
  6. dry with materialThe organic layer was dried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica column chromatography

Sources & evidence

ORD record
ord-4342890cfc164c2693919815cb20cdc5
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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