Ethanol → HCID 86757173, compound

HRID 1386480Notes

Reaction equation

HRID 1386480 reaction equation
[BH4-].[Na+].C([C:5]1[CH:6]=[CH:7][C:8]2[S:13][CH2:12][CH2:11][C:10]([CH3:15])([CH3:14])[C:9]=2[CH:16]=1)=O.[CH2:17]([OH:19])C>>[OH:19][CH2:17][CH:12]1[CH2:11][C:10]([CH3:14])([CH3:15])[C:9]2[CH:16]=[CH:5][CH:6]=[CH:7][C:8]=2[S:13]1

Participants

4

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 152843084,4-dimethyl-3,4-dihydro-2H-thiochromene-6-carbaldehyde

Product 1

HCID 86757173HCID 86757173, compoundYield 92%

Procedure

Sodium borohydride (NaBH4) (0.36 g, 9.7 mmol) is added at 0° C. to a solution of the previous 6-formyl-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran (2.00 g, 9.7 mmol) in 20 ml of ethanol. The agitation was continued at this temperature for 30 minutes. After evaporation of the ethanol, it is taken up again in 100 ml of ethyl ether and acidified by an aqueous 3N solution of HCl to pH 1. The mixture is extracted with ether, dried over MgSO4 filtered and the solvents evaporated. The crude product is purified by flash chromatography on silica (eluent petroleum ether:ethyl ether:100:10). 1.85 g of 6-(hydroxymethyl-4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyrane is obtained (gross yield=92%).

Workup

  1. customAfter evaporation of the ethanol, it
  2. extractionThe mixture is extracted with ether
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents evaporated
  6. customThe crude product is purified by flash chromatography on silica (eluent petroleum ether:ethyl ether:100:10)

Sources & evidence

ORD record
ord-8d0fbde100cb45c78e44000d6fd0bcd7
Source dataset
uspto-grants-2001_07
Patent number
US06265423B1

Reaction notes

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