Thiophene → (S)-3-Chloro-1-(thiophen-2-yl)propan-1-ol

HRID 1009839Notes

Reaction equation

HRID 1009839 reaction equation
S1C=CC=C1.ClCCC(Cl)=O.[Sn](Cl)(Cl)(Cl)Cl.[Cl:17][CH2:18][CH2:19][C:20]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)=[O:21].[BH4-].[Na+].ClCCC(C1SC=CC=1)O.C(OC=C)(=O)CCC>C1C=CC=CC=1.C(O)C.CCCCCC>[Cl:17][CH2:18][CH2:19][C@@H:20]([C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)[OH:21]

Participants

11

Reactant 7

HCID 8030Thiophene2×HCID 24287Tin tetrachlorideHCID 31247Vinyl butyrateHCID 693643-Chloropropionyl chlorideHCID 4311764Sodium borohydrideHCID 75678553-Chloro-1-(2-thienyl)-1-propanoneHCID 116583743-Chloro-1-(2-thienyl)-1-propanol

Product 1

HCID 10236042(S)-3-Chloro-1-(thiophen-2-yl)propan-1-ol

Reagents, catalysts & solvents 3

HCID 241BenzeneSolventHCID 702EthanolSolventHCID 8058HexaneSolvent

Procedure

Huiling et al. describe a preparation of (S)-(−)-3-N-methylamino-1-(2-thienyl)-1-propanol from thiophene. Thiophene is converted with 3-chloropropanoyl chloride in the presence of tin tetrachloride in benzene to 3-chloro-1-(2-thienyl)-1-propanone, which is reduced with sodium borohydride in ethanol to 3-chloro-1-(2-thienyl)-1-propanol. Kinetic resolution by transesterification using vinyl butanoate and lipase B from Candida antarctica as catalyst in hexane yielded (S)-3-chloro-1-(2-thienyl)-1-propanol, which is converted to (S)-3-iodo-1-(2-thienyl)-1-propanol using sodium iodide in acetone. Subsequent treatment with methylamine in tetrahydrofuran afforded (S)-(−)-3-N-methylamino-1-(2-thienyl)-1-propanol.

Sources & evidence

ORD record
ord-57f06b267ed14abbb7f922ec914cd0e9
Source dataset
uspto-grants-2011_07
Patent number
US07973182B2

Reaction notes

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