Dimethylformamide → 2-Methylpentane

HRID 471062Notes

Reaction equation

HRID 471062 reaction equation
CC1(C)[CH2:7][CH2:6][CH2:5][C:4]([CH3:9])([CH3:8])N1.C([Li])CCC.[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][OH:25])=[CH:19][CH:18]=1.CN([CH:29]=[O:30])C>O1CCCC1>[CH3:7][CH2:6][CH2:5][CH:4]([CH3:9])[CH3:8].[F:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][OH:25])=[CH:19][C:18]=1[CH:29]=[O:30]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 130352,2,6,6-TetramethylpiperidineHCID 820684-Fluorophenethyl AlcoholHCID 178418339Butyllithium

Product 2

HCID 78922-MethylpentaneHCID 579893302-Fluoro-5-(2-hydroxyethyl)benzaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2,2,6,6-Tetramethylpiperidine (3.0 g) was added dropwise to a stirred solution of n-butyllithium (1.6M in hexanes, 13 mL) in dry tetrahydrofuran (12 mL) at −78° C. After 10 min, 2-(4-fluorophenyl)ethanol (1.00 g) was added dropwise. The reaction mixture was stirred at −78° C. for 5 h and then dry DMF (3.18 mL) was added dropwise over 5 min. The cooling bath was removed and the reaction mixture allowed to warm to room temperature overnight. Ethyl acetate and aqueous HCl (2M) were added and the solution separated. The ethyl acetate layer was washed with water, brine, dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with ethyl acetate:isohexane, 1:1 to give the subtitled compound as an oil. Yield 0.43 g.

Workup

  1. customThe cooling bath was removed
  2. temperatureto warm to room temperature overnight
  3. additionEthyl acetate and aqueous HCl (2M) were added
  4. customthe solution separated
  5. washThe ethyl acetate layer was washed with water, brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customPurification
  10. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-9715754199764156bdb22ced397a759b
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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