Diisopropyl Ether → HCID 10890457, compound

HRID 1385547Notes

Reaction equation

HRID 1385547 reaction equation
[CH2:1]([C:6]1[CH:7]([OH:11])[CH2:8][CH2:9][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH3:5].C[C:13](C)([C:17]([O-:19])=[O:18])[C:14]([O-:16])=O.[CH:21](OC(C)C)(C)C>>[C:17]([O:19][CH3:21])(=[O:18])[CH2:13][C:14]([O:11][C@@H:7]1[CH2:8][CH2:9][CH:10]=[C:6]1[CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:16]

Participants

4

Reactant 3

HCID 7914Diisopropyl EtherHCID 6946994DimethylmalonatHCID 110948512-Cyclopenten-1-ol, 2-pentyl-

Product 1

HCID 10890457HCID 10890457, compound

Conditions

Temperature
21.5 °C

Procedure

A suspension of racemic 2-(pentyl)-2-cyclopenten-1-ol (100 mg; 0.649 mmol), dimethylmalonate (100 mg; 0.757 mmol), ground KHCO3 (7 mg; 0.05 mmol), diisopropyl ether (1.8 ml) and lipase (100 mg) was stirred in a 10 ml flask at room temperature (20-23° C.). Results are shown in the table below. The reaction was followed by GC method and the ee was determined by treating samples collected at the times indicated with N-methyl-N-trimethylsilyl-trifluoracetamide in dipropyl ether to silylate unreacted alcohol and effecting a chiral GC analysis (Megadex 5).

Workup

  1. customResults
  2. additionby treating samples
  3. customcollected at the times

Sources & evidence

ORD record
ord-26f2e75ce4cb41e79b0435e83fce1636
Source dataset
uspto-grants-2001_07
Patent number
US06262288B1

Reaction notes

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