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

HRID 48557Notes

Reaction equation

HRID 48557 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), followed by addition of vinyl acetate (2.6 g, 30 mmol) and finally Lipase PS 30 (69 mg, purchased from (Amano, Lombard, Ill.). 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-19b0a6cd0c464e5499abfb34662ee25b
Source dataset
uspto-grants-2004_03
Patent number
US06703394B2

Reaction notes

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