Methyl benzilate → HCID 67195729, compound

HRID 551380

Reaction equation

HRID 551380 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].C[O:10][C:11](=O)[C:12]([OH:25])([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[Na]>C1(C)C=CC=CC=1>[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][O:8][C:11](=[O:10])[C:12]([OH:25])([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 66159Methyl benzilateHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 5360545Sodium

Product 1

HCID 67195729HCID 67195729, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

((S)-1-Methyl-pyrrolidin-2-yl)-methanol (2.38 ml, 20 mmol) and hydroxy-diphenyl-acetic acid methyl ester (7.27 g, 30 mmol) are suspended in toluene (20 ml). Molecular sieve 4A (3 g) is added and the suspension is heated under stirring to 80° C. Sodium (0.46 g, 20 mmol) is added and the reaction mixture stirred at 80° C. for 3 hours. The reaction mixture is cooled to room temperature, solid filtered off, and washed with toluene. The filtrate is washed once with saturated aqueous NaHCO3 solution (50 ml) and twice with aqueous HCl 1M (30 ml each). The combined acidic aqueous layers are adjusted to pH 8 with saturated aqueous NaHCO3 solution. The emulsion is extracted with ethyl acetate (50 ml). The combined ethyl acetate layers are dried over sodium sulphate, filtered off and evaporated to dryness to give the product as a yellow oil that crystallises on standing. (M+H)+:326.2

Workup

  1. temperaturethe suspension is heated
  2. stirringthe reaction mixture stirred at 80° C. for 3 hours
  3. temperatureThe reaction mixture is cooled to room temperature
  4. filtrationsolid filtered off
  5. washwashed with toluene
  6. washThe filtrate is washed once with saturated aqueous NaHCO3 solution (50 ml) and twice with aqueous HCl 1M (30 ml each)
  7. extractionThe emulsion is extracted with ethyl acetate (50 ml)
  8. dry with materialThe combined ethyl acetate layers are dried over sodium sulphate
  9. filtrationfiltered off
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-efcf2f2a0b954f2e834f33ea46987872
Source dataset
uspto-grants-2011_05
Patent number
US07947730B2

Linked notes

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