Hydrochloric Acid → HCID 178526187, compound

HRID 236438Notes

Reaction equation

HRID 236438 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:13]([OH:15])=[S:14].C(=O)([O-])[O-].[Na+].[Na+].[BH4-].[Na+].Cl>C(OCC)(=O)C.C(COC)OC.O>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([OH:22])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:13]([OH:15])=[S:14]

Participants

8

Reactant 4

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

Product 1

HCID 178526187HCID 178526187, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 3.61 g. of 8-(2-furyl)-8-oxo-2-phenylthiooctanoic acid, 5.45 ml. of 1M aqueous sodium carbonate, 25 ml. of water and 15 ml. of glyme is added 0.41 g of sodium borohydride in portions during one minute. The resulting mixture is stirred at ambient temperature for 3.5 hours, diluted with ethyl acetate and acidified cautiously at 0°-10° C. with dilute hydrochloric acid. The organic layer is washed with water and brine, dried and evaporated, giving 3.54 g. of the product as an oil identified by its PMRδ4.800 (1, t, J=7).

Workup

  1. washThe organic layer is washed with water and brine
  2. customdried
  3. customevaporated
  4. customgiving 3.54 g

Sources & evidence

ORD record
ord-ea977348859c415aae8c0a98a64d317b
Source dataset
uspto-grants-1987_02
Patent number
US04644079

Reaction notes

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