Sodium borohydride → HCID 86642842, compound

HRID 1667780Notes

Reaction equation

HRID 1667780 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([CH:13]=[O:14])[CH:3]=1.[BH4-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][S:9]([CH3:12])(=[O:11])=[O:10])=[C:4]([CH2:13][OH:14])[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86642841HCID 86642841, compound

Product 1

HCID 86642842HCID 86642842, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 0.760 g (3.49 mmole) of methanesulfonic acid 4-fluoro-2-formyl-phenyl ester and 10 mL of methanol at 0 degrees was added, portionwise over 10 minutes, 0.200 g (5.4 mmole) of sodium borohydride. The mixture was stirred at 0 degrees for 10 minutes and then concentrated under reduced pressure. The residue was partitioned between 50 mL of ethyl acetate and 50 mL of water while 1 M hydrochloric acid was carefully added. The mixture was stirred at room temperature until gas evolution ceased. The aqueous layer was extracted three times with 20 mL of ethyl acetate. The combined organic layers were washed with 30 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give 0.740 g of methanesulfonic acid 4-fluoro-2-hydroxymethyl-phenyl ester as a yellow oil.

Workup

  1. additionwas added, portionwise over 10 minutes
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was partitioned between 50 mL of ethyl acetate and 50 mL of water while 1 M hydrochloric acid
  4. additionwas carefully added
  5. stirringThe mixture was stirred at room temperature until gas evolution
  6. extractionThe aqueous layer was extracted three times with 20 mL of ethyl acetate
  7. washThe combined organic layers were washed with 30 mL of brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-80ef070b203940da93826c904c0677ab
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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