Hydrochloric Acid → HCID 178519700, compound

HRID 126744Notes

Reaction equation

HRID 126744 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([OH:16])=[S:15])=[O:7].[C:23](=O)([O-])[O-:24].[Na+].[Na+].[BH4-].[Na+].Cl>COCCOC.C(OCC)(=O)C.O>[O:24]1[CH:23]=[CH:5][CH:4]=[C:3]1[C:2]([CH:6]([OH:7])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([OH:16])=[S:15])=[O:1]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 178520601HCID 178520601, compound

Product 1

HCID 178519700HCID 178519700, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3.61 g of 7-(2-furoyl)-2-phenylthioheptanoic acid in 15 ml of DME is added 25 ml of water and 5.45 ml of 1.0 M aqueous sodium carbonate. The resulting solution is treated furing 1 min. with 0.41 g of sodium borohydride in small portions. The mixture is stirred at ambient temperature for 3.5 hours, diluted with ethyl acetate, cooled to 0°, and treated with 4 M hydrochloric acid. The ethyl acetate layer is washed with water and brine, dried over MgSO4, and concentrated to give an oil.

Workup

  1. temperaturecooled to 0°
  2. washThe ethyl acetate layer is washed with water and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give an oil

Sources & evidence

ORD record
ord-060306e5919949db831969b85b8e3e80
Source dataset
uspto-grants-1981_03
Patent number
US04254036

Reaction notes

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