Thiochroman-4-one → 3,4-Dihydro-2H-1-benzothiopyran-4-ol

HRID 256418Notes

Reaction equation

HRID 256418 reaction equation
[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[CH2:3][CH2:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].OCC1(CC2C=CC=CC=2O)CCCCC1>>[S:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([OH:11])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 19048Thiochroman-4-oneHCID 20163643HCID 20163643, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 3751023,4-Dihydro-2H-1-benzothiopyran-4-ol

Procedure

Reduction of thiochroman-4-one with lithium aluminum hydride by the method of Preparation O, Part (iii), affords thiochroman-4-ol in like manner. This is taken up in acetic acid containing a molar excess of acetic anhydride, the mixture heated at reflux for three hours, cooled, ethanol added to quench the excess anhydride and the mixture hydrogenated by the method of Example 11.

Sources & evidence

ORD record
ord-0ed15ad592464ddb8da349c6de037d0b
Source dataset
uspto-grants-1987_10
Patent number
US04703052

Reaction notes

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