Diethyl Ether → Dimethyl 2-(4-(diethoxymethyl)benzyl)-2-(4-(methylthio) benzyl)malonate

HRID 566511Notes

Reaction equation

[CH2:1]([O:3][CH:4]([O:21][CH2:22][CH3:23])[C:5]1[CH:20]=[CH:19][C:8]([CH2:9][CH:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:7][CH:6]=1)[CH3:2].[H-].[Na+].[CH3:26][S:27][C:28]1[CH:35]=[CH:34][C:31]([CH2:32]Cl)=[CH:30][CH:29]=1.CCOCC>CN(C=O)C>[CH2:22]([O:21][CH:4]([O:3][CH2:1][CH3:2])[C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C:10]([CH2:32][C:31]2[CH:34]=[CH:35][C:28]([S:27][CH3:26])=[CH:29][CH:30]=2)([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[CH:19][CH:20]=1)[CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product from Step 1 (1.42 g, 4.4 mmol) in DMF (14 mL) at 0° C. was added NaH (131 mg, 80% in mineral oil). After 1 h. 4-(methylthio)benzyl chloride (0.64 mL, 4.4 mmol) was added and the mixture was stirred a further 2 h at 0° C. Following a standard aqueous/Et2O work-up, the crude was purified by flash column (1:20 EtOAc/toluene) to give a colorless oil (1.92 g).

Workup

customthe crude was purified by flash column (1:20 EtOAc/toluene)

Sources & evidence

ORD record: ord-d319a28586c1422293aa2b9726263e87
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06174874B1

Reaction notes

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