Sodium borohydride → 3-Chloro-1-(2-thienyl)-1-propanol

HRID 1928584Notes

Reaction equation

HRID 1928584 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:10])[CH2:7][CH2:8][Cl:9].[BH4-].[Na+]>C(O)C>[Cl:9][CH2:8][CH2:7][CH:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[OH:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 75678553-Chloro-1-(2-thienyl)-1-propanone

Product 1

HCID 116583743-Chloro-1-(2-thienyl)-1-propanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

For example, a method is known wherein 1-(2-thienyl)-3-chloropropan-1-one is reduced using sodium borohydride in ethanol to obtain 3-chloro-1-(2-thienyl)-1-propanol, halogen exchange is subsequently conducted in acetone using sodium iodide to obtain 3-iodo-1-(2-thienyl)-1-propanol, and then this is reacted with a monomethylamine aqueous solution in tetrahydrofuran (CHIRALITY, 12, 26-29 (2000)). However, since the raw material used in this method is 1-(2-thienyl)-3-chloropropan-1-one, which is a very unstable compound, this method is not industrially applicable.

Sources & evidence

ORD record
ord-ddcac21f5e8844f2ac06dd98f579d4e8
Source dataset
uspto-grants-2012_05
Patent number
US08183392B2

Reaction notes

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