Dimethylformamide → HCID 20095713, compound

HRID 1770237Notes

Reaction equation

Br[C:2]1[C:3]([O:16][CH2:17][CH3:18])=[CH:4][C:5]([O:13][CH2:14][CH3:15])=[C:6]([O:9][CH2:10][O:11][CH3:12])[C:7]=1[CH3:8].C([Li])CCC.CN(C)[CH:26]=[O:27].[Cl-].[NH4+].C1C[O:34][CH2:33]C1>>[CH2:17]([O:16][C:3]1[C:4]([O:27][CH3:26])=[C:5]([O:13][CH2:14][CH3:15])[C:6]([O:9][CH2:10][O:11][CH3:12])=[C:7]([CH3:8])[C:2]=1[CH:33]=[O:34])[CH3:18]

Participants

Reactant 5

HCID 6228Dimethylformamide

HCID 8028Tetrahydrofuran

HCID 25517Ammonium Chloride

HCID 20095706HCID 20095706, compound

HCID 178418339Butyllithium

Product 1

HCID 20095713HCID 20095713, compound

Conditions

Temperature: -40 °C

Procedure

43.6 g of 5-bromo-2,4-diethoxy-6-methyl-1-methoxymethyloxybenzene prepared in Referential Example 8 was dissolved in 220 ml of THF, and 100 ml of n-butyllithium (1.6M n-hexane solution) was dropwise added thereto at -70° C. The mixture was stirred at -40° C. for 30 min, and 11.9 g of dimethylformamide was dropwise added thereto. The temperature of the reaction mixture was returned to room temperature, and an aqueous ammonium chloride solution was added thereto, followed by extracting with ethyl acetate. The organic phase was washed with-water, dried, concentrated and purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=90:10) to prepare 19.2 g of the product compound as a colorless oleaginous substance.

Workup

customat -70° C
customwas returned to room temperature
extractionby extracting with ethyl acetate
washThe organic phase was washed with-water
customdried
concentrationconcentrated
custompurified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=90:10)
customto prepare 19.2 g of the product compound as a colorless oleaginous substance

Sources & evidence

ORD record: ord-11f6dafab42942d3ac681268926aac1c
Source dataset: uspto-grants-1995_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05385942

Reaction notes

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