Tetrahydrofuran → 9-Benzyloxy-1-(2-methyl-pyrimidin-5-yl)-non-1-en-4-one

HRID 2120682Notes

Reaction equation

HRID 2120682 reaction equation
COP([CH2:7][C:8](=[O:22])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=O)OC.[CH3:23][C:24]1[N:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][N:25]=1.[C:32](=O)([O-])[O-].[K+].[K+].C1COCC1>C(OCC)(=O)C>[CH2:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:8](=[O:22])[CH2:7][CH:32]=[CH:30][C:27]1[CH:26]=[N:25][C:24]([CH3:23])=[N:29][CH:28]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 31609702-Methylpyrimidine-5-carbaldehydeHCID 58765522(7-Benzyloxy-2-oxo-heptyl)-phosphonic acid dimethyl ester

Product 1

HCID 696665989-Benzyloxy-1-(2-methyl-pyrimidin-5-yl)-non-1-en-4-oneYield 100%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 11-2 (4.4 g, 13.8 mmol), 2-methyl-pyrimidine-5-carbaldehyde (1.5 g, 12.5 mmol; for preparation, see J. Heterocyclic Chem., 28, 1281 (1991)) potassium carbonate (3.1 g, 25 mmol) and THF (200 mL) was heated at 60° C. for 3 hours. Following cooling, the mixture was diluted with ethyl acetate, washed with sat. NaHCO3 and brine, and dried over magnesium sulfate. Evaporation of the solvents gave 4.0 g (100%) of 11-3 as a white solid.

Workup

  1. temperatureFollowing cooling
  2. washwashed with sat. NaHCO3 and brine
  3. dry with materialdried over magnesium sulfate
  4. customEvaporation of the solvents

Sources & evidence

ORD record
ord-3b35373817a640278191f1599c17c0c2
Source dataset
uspto-grants-2004_02
Patent number
US06693101B2

Reaction notes

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