HCID 13393800, compound → HCID 13393825, compound

HRID 978787Notes

Reaction equation

HRID 978787 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[S:5][CH:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:3]=1[CH:20]=[O:21]>CO.[BH4-].[Na+]>[Cl:1][C:2]1[C:11]2[C:6](=[C:7]([O:12][CH3:13])[CH:8]=[CH:9][CH:10]=2)[S:5][CH:4]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:3]=1[CH2:20][OH:21]

Participants

4

Reactant 1

HCID 13393800HCID 13393800, compound

Product 1

HCID 13393825HCID 13393825, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 4311764Sodium borohydrideSolvent

Procedure

As in example 14 but starting from 3.16 g 4-chloro-3-formyl-8-methoxy-thioflav-3-ene in 30 ml dry methanol and 0.35 g sodium borohydride. After work up, the crude oil is crystallized in a mixture of n-hexane and ethylacetate. Pure 4-chloro-3-hydroxymethyl-8-methoxy-thioflav-3-ene is obtained as yellow crystals; m.p. 143°-145° C.-TLC (SiO2, n-hexane CH2Cl2 1:1): Rf =0.05.

Workup

  1. customAfter work up, the crude oil is crystallized in a mixture of n-hexane and ethylacetate

Sources & evidence

ORD record
ord-0faec9e88e494b86a97358aaaa4eb42e
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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