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

HRID 2115276Notes

Reaction equation

HRID 2115276 reaction equation
[Cl:1][CH2:2][CH2:3][CH:4]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[OH:5].C1(=O)OC(=O)CC1>CC(OC)(C)C>[Cl:1][CH2:2][CH2:3][C@@H:4]([C:6]1[S:7][CH:8]=[CH:9][CH:10]=1)[OH:5]

Participants

4

Reactant 2

HCID 7922Succinic anhydrideHCID 116583743-Chloro-1-(2-thienyl)-1-propanol

Product 1

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

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

197 g (1.16 mol) of alcohol 4, containing 10% of alcohol 5 (i.e. the reaction product obtained from Example 1), are initially introduced in 1 liter of MTBE. 64.4 g (0.64 mol) of succinic anhydride and 10 g of Burkholderia plantarii lipase are then added. The mixture is stirred at RT for 20 h and freed from the enzyme by filtration. After 1.4 l of water have been added, the mixture is adjusted to pH=9 with sodium carbonate and the aqueous phase is separated off. The organic phase is dried over sodium sulfate and freed from the solvent. 96 g of 6, which contains approx. 10% of the corresponding antipode of 5, are obtained.

Workup

  1. filtrationfreed from the enzyme by filtration
  2. additionAfter 1.4 l of water have been added
  3. customthe aqueous phase is separated off
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. customare obtained

Sources & evidence

ORD record
ord-667fec5b05314c599ad8d2d3e23540a7
Source dataset
uspto-grants-2008_10
Patent number
US07435835B2

Reaction notes

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