Acetate → (R)-4,4-diethoxy-2-(hydroxymethyl)butyl acetate

HRID 1166704Notes

Reaction equation

HRID 1166704 reaction equation
[C:1]([O:4][CH:5]=[CH2:6])(=[O:3])[CH3:2].CCCC[CH2:11][CH3:12].[CH3:13][CH2:14][O:15][C:16]([CH3:18])=[O:17].C[C:20]([O-])=[O:21]>C(Cl)Cl>[C:1]([O:4][CH2:5][C@H:6]([CH2:18][CH:16]([O:17][CH2:11][CH3:12])[O:15][CH2:14][CH3:13])[CH2:20][OH:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 175AcetateHCID 7904Vinyl AcetateHCID 21226206Ethyl acetate hexane

Product 1

HCID 15060056(R)-4,4-diethoxy-2-(hydroxymethyl)butyl acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 10 ml 1 neck round bottom flask was charged the product of Example 14 step b) (3.84 g, 20 mmol), follows by addition of vinyl acetate (2.6 g, 30 mmol) and finally Lipase PS 30 (69 mg, purchased from Amano, Lombard, Illinois). The mixture was allowed to stir at ambient temperature for 16 hours. Progress of the reaction was closely monitored by TLC (2/1 hexane—EtOAc; stained with Ce2(SO4)3 and charred on hot plate; r.f. of diol is 0.1, monoacetate is 0.3, bis acetate is 0.75). The reaction mixture was diluted with CH2Cl2 and filtered through a 5 micron filter. The filter was washed with additional CH2Cl2. The filtrate was then concentrated in vacuo to afford the desired product.

Workup

  1. filtrationfiltered through a 5 micron
  2. filtrationfilter
  3. washThe filter was washed with additional CH2Cl2
  4. concentrationThe filtrate was then concentrated in vacuo

Sources & evidence

ORD record
ord-bd86af4312a742048ddc5c355bce01a6
Source dataset
uspto-grants-2003_09
Patent number
US06613936B1

Reaction notes

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