Chloromethyl methyl sulfide → HCID 66610387, compound

HRID 1404717Notes

Reaction equation

HRID 1404717 reaction equation
[CH3:1][S:2][CH2:3]Cl.[H-].[Na+].[CH2:7]([CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C)C=O>[CH2:7]([C:14]([CH2:3][S:2][CH3:1])([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 16916Chloromethyl methyl sulfideHCID 24758Sodium hydrideHCID 69090Diethyl 2-benzylpropanedioate

Product 1

HCID 66610387HCID 66610387, compoundYield 100.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
23 °C

Procedure

Chloromethyl methyl sulfide (1.4 mL, 17 mmol, 1.0 equiv) and 60% sodium hydride in mineral oil (750 mg, 19 mmol, 1.1 equiv) were sequentially added to a stirred solution of diethyl 2-benzylmalonate (4.0 mL, 17 mmol, 1.0 equiv) in N,N-dimethylformamide (34 mL) at 0° C. The resulting mixture was warmed to 23° C. and stirred for 18 h. The reaction mixture was concentrated under vacuum. The residue was diluted with water (150 mL) and extracted with diethyl ether (4×70 mL). The combined organic layers were dried (MgSO4), gravity-filtered, and concentrated by rotary evaporation to afford a yellow oil (5.3 g, 99%): 1H NMR (300 MHz, CDCl3) δ 7.13-7.30 (m, 5H), 4.22 (q, J=7 Hz, 4H), 3.36 (s, 2H), 2.94 (s, 2H), 2.11 (s, 3H), 1.27 (t, J=7 Hz, 6H).

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. additionThe residue was diluted with water (150 mL)
  3. extractionextracted with diethyl ether (4×70 mL)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationgravity-filtered
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-c0b55dffbfb04f99965feaa4f043c436
Source dataset
uspto-grants-2014_12
Patent number
US08912338B2

Reaction notes

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