Potassium borohydride → HCID 12747907, compound
Reaction equation
[Cl:1][C:2]1[C:13]([C:14](=[O:20])[C:15]2[S:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][C:5]2[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:21].[BH4-].[K+]>O>[Cl:1][C:2]1[C:13]([CH:14]([OH:20])[C:15]2[S:19][CH:18]=[CH:17][CH:16]=2)=[CH:12][C:5]2[CH2:6][CH:7]([C:9]([OH:11])=[O:10])[O:8][C:4]=2[C:3]=1[Cl:21]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
A magnetically stirred suspension of 3.4 g. (0.01 M) of 6,7-dichloro-2,3-dihydro-5-(2-thenoyl)-benzofuran-2-carboxylic acid and 100 ml. water is cooled to 5° C. in an icewater bath. A solution of 0.8 g. (0.0148 M) potassium borohydride and 20 ml. water is added dropwise to the above suspension over one-half hour. The resulting solution is stirred 2 hours at 25° C., filtered to remove some cloudiness and acidified with 6N HCl to give 6,7-dichloro-2,3-dihydro-5-[hydroxy-(2-thienyl)methyl]benzofuran-2-carboxylic acid as a yellow gum. The product is purified by precipitating it from 2N NaOH with 6N HCl. The aqueous solution is decanted from the gum which is triturated with 6N HCl to give a pale yellow solid. This solid is washed with water and air dried. It is then dried 24 hours at 25° C. and lmm Hg over P2O5.
Workup
- additionA magnetically stirred suspension of 3.4 g
- filtrationfiltered
- customto remove some cloudiness
Sources & evidence
- ORD record
- ord-774e28b08b144e3ab946a88d53b7aade
- Source dataset
- uspto-grants-1978_07
- Patent number
- US04100294
Reaction notes
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