Methyl 4-oxobutyrate → Dimethyl 3-formyl-4-hydroxyheptanedioate

HRID 593415

Reaction equation

HRID 593415 reaction equation
[O:1]=[CH:2][CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6]>CN(C=O)C>[CH:2]([CH:3]([CH:2]([OH:1])[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])[CH2:4][C:5]([O:7][CH3:8])=[O:6])=[O:1]

Participants

3

Reactant 1

HCID 83779Methyl 4-oxobutyrate

Product 1

HCID 123250817Dimethyl 3-formyl-4-hydroxyheptanedioate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

(S)-Proline (14.9 mg, 0.13 mmol) was added to a stirred solution of 16 (150 mg, 1.29 mmol) in THF (650 μl). The reaction mixture was stirred at r.t. for 14 h. The reaction mixture was purified directly by column chromatography, eluting with petrol/EtOAc (2:1), to give the aldehydes 17 and SI-3 (as a 3.6:1 mixture of anti:syn diastereoisomers, 91 mg, 61%) as a clear colourless oil. The reaction was also conducted on a 244 mg scale of aldehyde 16 in DMF which gave a 2:1 ratio of anti:syn diastereoisomers (100 mg, 41%).

Workup

  1. additionas a 3.6:1 mixture of anti
  2. customgave a 2:1 ratio of anti

Sources & evidence

ORD record
ord-e39d86288885447bbe8053d407512a87
Source dataset
uspto-grants-2016_01
Patent number
US09242954B2

Linked notes

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