Water → HCID 22012207, compound

HRID 378546Notes

Reaction equation

HRID 378546 reaction equation
[C:1]([O:8][CH3:9])(=[O:7])[CH2:2][C:3]([O:5][CH3:6])=[O:4].CC(C)([O-])C.[K+].CS(O[CH2:21][CH:22]1[C:26]2[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=2[O:24][CH2:23]1)(=O)=O.O>CN1C(=O)CCC1>[F:31][C:28]1[CH:29]=[CH:30][C:25]2[O:24][CH2:23][CH:22]([CH2:21][CH:2]([C:1]([O:8][CH3:9])=[O:7])[C:3]([O:5][CH3:6])=[O:4])[C:26]=2[CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7943Dimethyl malonateHCID 22012215HCID 22012215, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 22012207HCID 22012207, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent2×

Conditions

Temperature
60 °C

Procedure

Dimethyl malonate (262 g) was dissolved in NMP (2 l) and potassium tert-butoxide (202 g) was added portionwise keeping the temperature at 15-20° C. The mixture was heated to 60° C. and a solution of 2,3-dihydro-5-fluorobenzofuran-3-ylmethyl methanesulfonate (155 g) in NMP (150 ml) was added dropwise. The mixture was stirred for 4 h at 70-75° C. followed by addition of cold water. Extraction with ether, drying the ether phase over magnesium sulfate, followed by removal of solvent in vacuo gave dimethyl 2-(2,3-dihydro-5-fluorobenzofuran-3-ylmethyl)malonate (160 g) as an oil, which was sufficiently pure for the further synthesis.

Workup

  1. customat 15-20° C
  2. extractionExtraction with ether
  3. dry with materialdrying the ether phase over magnesium sulfate
  4. customfollowed by removal of solvent in vacuo

Sources & evidence

ORD record
ord-4c705bb56bb14c02895d91256426e3bc
Source dataset
uspto-grants-2000_02
Patent number
US06031099

Reaction notes

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