Sodium hydride → HCID 19767474, compound

HRID 1590607Notes

Reaction equation

HRID 1590607 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8].[H-].[Na+].Cl[CH2:23][O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:9]([CH2:23][O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=2)([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109212541-[(Chloromethoxy)methyl]-4-methoxybenzeneHCID 19767513Diethyl 3,4-difluorophenylmalonate

Product 1

HCID 19767474HCID 19767474, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of diethyl 3,4-difluorophenylmalonate (13 g, 48 mmol) in dry tetrahydrofuran (100 ml) at 0° C. under a nitrogen atmosphere was added sodium hydride (1.5 g, 50 mmol) of 80% oil dispersion). The mixture was allowed to warm to room temperature and then heated to reflux for 1hour. To the cooled mixture was added 4-methoxybenzyl chloromethyl ether (9.5 g, 51 mmol ref. Synthesis, 1983, 762) and reflux was continued overnight. The cooled mixture was partitioned between water and diethyl ether, the organic layer was separated, dried over anhydrous magnesium sulphate and evaporated to leave diethyl 2-(3,4-difluorophenyl)-2(4-methoxybenzyloxymethyl)malonate as a yellow oil Nmr δ7.35 (1H,m), 7.2 (2H,d), 7.15-7.00 (2H,m), 6.85 (2H,d), 4.45 (2H,s), 4.20 (4H,q), 4.10 (2H,s), 3.80 (3H,s), 1.25 (6H,t).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1hour
  3. temperaturereflux
  4. customThe cooled mixture was partitioned between water and diethyl ether
  5. customthe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-be065ddd98404843bd897c584d9422c3
Source dataset
uspto-grants-1993_04
Patent number
US05204333

Reaction notes

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