Toluene → HCID 22494918, compound

HRID 1816531Notes

Reaction equation

HRID 1816531 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]([O:5][CH2:6][C:7]1[C:8]2[C:15](C)=[CH:14][CH:13]=[CH:12][C:9]=2[S:10][CH:11]=1)=[O:4].[C:19]1(C)C=CC=CC=1>>[F:18][C:2]([F:1])([F:17])[C:3]([O:5][CH2:6][C:7]1[C:8]2[CH:15]=[CH:14][C:13]([CH3:19])=[CH:12][C:9]=2[S:10][CH:11]=1)=[O:4]

Participants

3

Reactant 2

HCID 1140TolueneHCID 11208073HCID 11208073, compound

Product 1

HCID 22494918HCID 22494918, compound

Procedure

A mechanical stirrer, a 200-mL dropping funnel and an internal thermometer were attached to a 3000-mL three neck flask. A solution obtained by dissolving the mixture (300.00 g) of the (4-methylbenzo[b]thiophen-3-yl)methyl 2,2,2-trifluoroacetate and the (6-methylbenzo[b]thiophen-3-yl)methyl 2,2,2-trifluoroacetate obtained by the reaction in Example 3 in 1500 mL of toluene was introduced into the flask, which was dipped in a water bath. Into the flask, was introduced 30.00 g of sodium borohydride. Methanol (150 mL) was introduced into the dropping funnel. The dropping was carried out for 60 minutes, and the mixture was intactly stirred at room temperature for 60 minutes. Water (1000 mL) was added to the flask and the resulting mixture was filtered through Celite. An organic layer was separated from an aqueous layer, and the aqueous layer was extracted with 500 mL of toluene. The organic layer was washed with 1000 mL of a saturated brine twice. The organic layers were dried with anhydrous magnesium sulfate, filtered and concentrated to obtain a yellow oil, a mixture (295.12 g) of the (4-methylbenzo[b]thiophen-3-yl)methan-1-ol and the (6-methylbenzo[b]thiophen-3-yl)methan-1-ol.

Workup

  1. customA mechanical stirrer, a 200-mL dropping
  2. customA solution obtained

Sources & evidence

ORD record
ord-45d15719d701458990dbb97e0023add6
Source dataset
uspto-grants-2005_04
Patent number
US06884896B2

Reaction notes

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