Dimethylformamide → HCID 21187834, compound

HRID 1383555Notes

Reaction equation

HRID 1383555 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8][CH3:9])=[C:4]([O:10][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:3]=1.C([Li])CCC.CN(C)[CH:23]=[O:24].B(F)(F)F.CCOCC>O1CCCC1.CCCCCC>[CH:11]1([O:10][C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][C:5]=2[S:8][CH3:9])[CH:23]=[O:24])[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8000Boron trifluoride etherateHCID 21187828HCID 21187828, compoundHCID 178418339Butyllithium

Product 1

HCID 21187834HCID 21187834, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of 4-bromo-2-cyclopentyloxy-1-(methylthio)benzene (13.2 g) in dry tetrahydrofuran (100 mL) under nitrogen is treated at −70° C. with a solution of butyllithium in hexane (20.24 mL; 2.5 M) and the resulting solution is stirred for 1 hour at this temperature. It is then treated with dimethylformamide (7.12 mL), followed by boron trifluoride diethyl etherate (11.32 mL), keeping the temperature at −65° C. When the addition is complete the reaction mixture is allowed to warm to room temperature and is then poured into ice-water (450 ml,) and extracted with dichloromethane (3×400 mL). The combined extracts are dried over magnesium sulfate and concentrated to give an oil, which is subjected to flash chromatography, eluting with a mixture of dichloromethane and cyclohexane (3:7 v/v), to give 3-cyclopentyloxy-4-(methylthio)-benzaldehyde (6.2 g). [NMR(DMSO): 9.91(S,1H),7.53(dd,1H),7.36(d,1H), 7.33(d,1H),5.01 (m,1H),2.44(s,3H),2.0-1.5(m,8H)].

Workup

  1. customat −65° C
  2. additionWhen the addition
  3. extractionextracted with dichloromethane (3×400 mL)
  4. dry with materialThe combined extracts are dried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give an oil, which
  7. washeluting with a mixture of dichloromethane and cyclohexane (3:7 v/v)

Sources & evidence

ORD record
ord-83e5af04f6d04c01bb226815d38f6524
Source dataset
uspto-grants-2001_07
Patent number
US06255326B1

Reaction notes

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