Diketene → HCID 11513976, compound

HRID 1184024Notes

Reaction equation

HRID 1184024 reaction equation
[C:1]1([C@H:7]([OH:9])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:10]=[C:11]1[O:14][C:13](=[O:15])[CH2:12]1>O1CCCC1.CN(C1C=CN=CC=1)C>[O:14]=[C:11]([CH3:10])[CH2:12][C:13]([O:9][C@@H:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH3:8])=[O:15]

Participants

5

Reactant 2

HCID 12661DiketeneHCID 6375161-Phenylethanol, (R)-

Product 1

HCID 11513976HCID 11513976, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1-phenylethanol (6.0 ml, 50 mmol) in dry tetrahydrofuran (75 ml) at room temperature was added 4-(N,N-dimethylamino)pyridine (610 mg, 5.0 mmol) followed by dropwise addition of 4-methyleneoxetan-2-one (3.83 ml, 50 mmol). The reaction was stirred for 12 hours at room temperature, then the solvent removed under reduced pressure. The residue was dissolved in ethyl acetate, poured into a separatory funnel, and washed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate, then brine. The organic phase was separated and the solvent removed under resuced pressure to provide (R)-1-phenylethyl 3-oxobutanoate as a light reddish oil (10.3 g, 100%). 1H NMR (CDCl3, 400 MHz) δ 7.4-7.2 (m, 5H); 5.94 (q, 1H, J=6.6 Hz); 3.45 (s, 2H); 2.22 (s, 3H); 1.56 (d, 3H, J=6.6 Hz).

Workup

  1. customthe solvent removed under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. additionpoured into a separatory funnel
  4. washwashed with 1M aqueous hydrochloric acid, water, saturated aqueous sodium bicarbonate
  5. customThe organic phase was separated
  6. customthe solvent removed under resuced pressure

Sources & evidence

ORD record
ord-fae3b861a92f40fe8e5bc03001f00913
Source dataset
uspto-grants-2014_03
Patent number
US08664399B2

Reaction notes

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