Hydrochloric Acid → HCID 54074270, compound

HRID 371119Notes

Reaction equation

HRID 371119 reaction equation
[C:1]([C:4]([Cl:11])=[CH:5][CH2:6][C:7]([O:9][CH3:10])=[S:8])(O)=[O:2].C(Cl)(=O)OCC.[BH4-].[Na+].Cl>C1COCC1.N1C=CC=CC=1>[OH:2][CH2:1][C:4]([Cl:11])=[CH:5][CH2:6][C:7]([O:9][CH3:10])=[S:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 54059155HCID 54059155, compound

Product 1

HCID 54074270HCID 54074270, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl (2-carboxy-2-chlorovinyl)thioacetate (1) (1.48 g), pyridine (0.65 ml), and ethyl chlorocarbonate (0.6 ml) is stirred in THF at -30° C. for 5 minutes and subsequently at 0° C. for 10 minutes. Sodium borohydride (0.8 g) is added thereto, and the mixture is stirred at 0° C. for 2 hours. The reaction mixture is poured into dil. HCl and extracted with ethyl acetate. The ethyl acetate extract is washed with water, concentrated in vacuo, and chromatographed over silica gel to give methyl (2-hydroxymethyl-2-chlorovinyl)thioacetate (2). Yield: 492 mg.

Workup

  1. extractionextracted with ethyl acetate
  2. extractionThe ethyl acetate extract
  3. washis washed with water
  4. concentrationconcentrated in vacuo
  5. customchromatographed over silica gel

Sources & evidence

ORD record
ord-233e920e5aed4a77bc6dd9f1b2f8f084
Source dataset
uspto-grants-1985_07
Patent number
US04529721

Reaction notes

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