Diethyl Ether → N-o-methoxybenzoyl-L-prolinal diethyl acetal

HRID 467153Notes

Reaction equation

HRID 467153 reaction equation
Cl.[CH2:2]([O:4][CH:5]([O:11][CH2:12][CH3:13])[C@@H:6]1[CH2:10][CH2:9][CH2:8][NH:7]1)[CH3:3].[C:14](Cl)(=[O:23])[C:15]1[C:16]([O:21][CH3:22])=[CH:17][CH:18]=[CH:19][CH:20]=1.C(N(CC)CC)C.CCOCC>C(Cl)Cl>[CH2:12]([O:11][CH:5]([O:4][CH2:2][CH3:3])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:14](=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[O:21][CH3:22])[CH3:13]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 889692-Methoxybenzoyl chlorideHCID 86746304L-prolinal diethyl acetal hydrochloride

Product 1

HCID 15132643N-o-methoxybenzoyl-L-prolinal diethyl acetalYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

L-prolinal diethyl acetal hydrochloride is dissolved, together with the o-anisoyl chloride (853 mg, 4.01 mmol), in methylene chloride (12 ml), and triethylamine (1.7 ml, 12.2 mmol) is added dropwise thereto under ice-cooling and agitation. After the dropwise addition, stirring is further continued for 30 minutes under cooling and then for one hour and a half at room temperature. Ether (40 ml) is added to the reaction mixture, and the ethereal layer is separated, washed with a saturated aqueous solution of sodium hydrogen carbonate and a saturated aqueous solution of edible salt, dried over sodium sulfate and filtrated. The filtrate is concentrated to dryness under reduced pressure. The residue is purified by column chromatography on silica gel (n-hexane-ethyl acetate, 2:1) to give 952 mg (75%) of the title compound as a pale yellow syrup.

Workup

  1. temperatureunder ice-cooling
  2. additionAfter the dropwise addition
  3. temperatureunder cooling
  4. waitfor one hour
  5. customat room temperature
  6. customthe ethereal layer is separated
  7. washwashed with a saturated aqueous solution of sodium hydrogen carbonate
  8. dry with materiala saturated aqueous solution of edible salt, dried over sodium sulfate
  9. filtrationfiltrated
  10. concentrationThe filtrate is concentrated to dryness under reduced pressure
  11. customThe residue is purified by column chromatography on silica gel (n-hexane-ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-0bd8a77cb2204cf3a40b700f766ac7ae
Source dataset
uspto-grants-1992_10
Patent number
US05158970

Reaction notes

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