Sodium hydride → (S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid benzyl ester

HRID 1628150Notes

Reaction equation

HRID 1628150 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1)[CH3:2].[H-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])[C@@H:5]([O:14][CH2:15][CH3:16])[CH2:6][C:7]1[CH:8]=[CH:9][C:10]([OH:13])=[CH:11][CH:12]=1)[C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 9816147Ethyl (2S)-2-ethoxy-3-(4-hydroxyphenyl)propanoate

Product 1

HCID 66864807(S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid benzyl esterYield 186.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(S)-2-Ethoxy-3-(4-hydroxy-phenyl)-propionic acid ethyl ester (8.1 g, 34 mmol) was dissolved in benzylic alcohol (14.7 g, 135 mmol) and freshly washed sodium hydride (1.63 g, 41 mmol) was caustiosuly added under nitrogen atmosphere. The resulting mixture was warmed up to 50° C. under vacuum and after 6 h toluene was added and the mixture was extracted with aq. KHSO4 (2N). The combined organic layers were dried and evaporated under high vacuum at 70° C. to afford title compound as an oil (9.51 g, 93.1%). 1H NMR (400 MHz, CDCl3): δ 7.19-7.40 (m, 5H), 7.03-7.06 (d, 2H), 6.68-6.71 (d, 2H), 5.14 (s, 2H), 4.03-4.06 (t, 1H), 3.57-3.61 (m, 1H), 3.36-3.40 (m, 1H), 2.97 (s, 1H), 1.14-1.18 (t, 3H).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with aq. KHSO4 (2N)
  3. customThe combined organic layers were dried
  4. customevaporated under high vacuum at 70° C.

Sources & evidence

ORD record
ord-55d3a7bf3ce24fbbaae6f9c70a98c404
Source dataset
uspto-grants-2014_07
Patent number
US08785681B2

Reaction notes

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