tert-Butanol → HCID 13393820, compound

HRID 978788Notes

Reaction equation

HRID 978788 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].CC(=CC)C.C([OH:31])(C)(C)C>>[C:20]([C:3]1[CH:4]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[S:5][C:6]2[C:11]([C:2]=1[Cl:1])=[CH:10][CH:9]=[CH:8][C:7]=2[O:12][CH3:13])([OH:31])=[O:21]

Participants

4

Reactant 3

HCID 6386tert-ButanolHCID 105532-Methyl-2-buteneHCID 13393800HCID 13393800, compound

Product 1

HCID 13393820HCID 13393820, compound

Procedure

As in example 13 but starting from 3.16 g of 4-chloro-3-formyl-8-methoxy-thioflav-3-ene, 250 ml tert-butanol and 60 ml 2-methyl-2-butene. After work up the crude oil is crystallised in a mixture of n-hexane and ethyl acetate. Pure 3-carboxy-4-chloro-8-methoxy-thioflav-3-ene is obtained as yellow crystals; m.p. 207°-210° C.-TLC (SiO2, CH2Cl2 /Acetone/HCOOH 18/1/1): Rf =0.45.

Workup

  1. customAfter work up the crude oil is crystallised in a mixture of n-hexane and ethyl acetate

Sources & evidence

ORD record
ord-0d2eed7d374b4776bc0d4ec567097371
Source dataset
uspto-grants-1987_05
Patent number
US04665202

Reaction notes

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