Dimethylformamide → HCID 21187871, compound

HRID 1870424Notes

Reaction equation

HRID 1870424 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13][CH3:14])=[C:9]([O:15][CH:16]([CH3:18])[CH3:17])[CH:8]=1.CN(C)[CH:21]=[O:22].B(F)(F)F.CCOCC>O1CCCC1.O>[CH3:14][S:13][C:10]1[CH:11]=[CH:12][C:7]([CH:21]=[O:22])=[CH:8][C:9]=1[O:15][CH:16]([CH3:18])[CH3:17]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8000Boron trifluoride etherateHCID 21187832HCID 21187832, compoundHCID 178418339Butyllithium

Product 1

HCID 21187871HCID 21187871, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of n-butyllithium in hexanes (14.82 mL; 2.5M) is added to a solution of 4-bromo-2-prop-2-yloxythioanisole (8.8 g) in dry tetrahydrofuran (70 mL), whilst cooling the mixture to -70° C. under nitrogen. The mixture is stirred for 1 hour at -70° C. Dry dimethylformamide (5.22 mL) and boron trifluoride diethyl etherate (8.29 mL) are added sequentially and the mixture is allowed to warm to room temperature. The mixture is poured into water and the product is extracted with dichloromethane. The extract is dried over magnesium sulfate and concentrated in vacuo, and the residue is subjected to flash chromatography on silica gel, eluting with a mixture of pentane and ethyl acetate (9:1 v/v) to give 4-methylthio-3-prop-2-yloxybenzaldehyde, in the form of a soft yellow solid, m.p. 50-54° C.

Workup

  1. temperatureto warm to room temperature
  2. extractionthe product is extracted with dichloromethane
  3. dry with materialThe extract is dried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. washeluting with a mixture of pentane and ethyl acetate (9:1 v/v)

Sources & evidence

ORD record
ord-a6e080bbe78642abaeabc9a6f2abd24c
Source dataset
uspto-grants-2000_08
Patent number
US06096768

Reaction notes

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