Dimethylformamide → Ethyl 3-phenyl-2-hydroxy-2-ethoxycarbonyl-propanoate

HRID 1526506Notes

Reaction equation

HRID 1526506 reaction equation
[CH2:1]([CH:8]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[Cs+].CN(C=[O:25])C>>[CH2:1]([C:8]([OH:25])([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 25953Cesium fluorideHCID 69090Diethyl 2-benzylpropanedioate

Product 1

HCID 15828909Ethyl 3-phenyl-2-hydroxy-2-ethoxycarbonyl-propanoate

Conditions

Temperature
40 °C

Procedure

A mixture of diethyl benzylpropanedioate (41 g) and CsF (49.8 g) in 90 mL of DMF was heated at 40° C. with vigorous air bubbling for 3 days. The resulting mixture was diluted with ethyl acetate (800 mL) and washed with water (3×1 L). The organic layer was concentrated and then purified by Biotage silica gel column chromatography (5-20% ethyl acetate in hexanes) to give the title product as a colorless oil. 1H NMR (300 MHz, CDCl3) δ: 7.22-7.26 (m, 5H), 4.23 (q, J=7.2 Hz, 4H), 3.80 (br, 1H), 3.35 (s, 2H), 1.26 (t, J=7.2 Hz, 6H).

Workup

  1. custombubbling for 3 days
  2. additionThe resulting mixture was diluted with ethyl acetate (800 mL)
  3. washwashed with water (3×1 L)
  4. concentrationThe organic layer was concentrated
  5. custompurified by Biotage silica gel column chromatography (5-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-7d16928b70f44c9699e03c981cf62f1d
Source dataset
uspto-grants-2015_07
Patent number
US09085568B2

Reaction notes

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