Formaldehyde → HCID 68434734, compound

HRID 2222860Notes

Reaction equation

HRID 2222860 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:9])=[CH:4][CH:3]=1.C1([Li])C=CC=CC=1.[CH2:24]=[O:25].O>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]([NH:10][C:11](=[O:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH3:9])=[C:6]([CH:7]=1)[CH2:24][OH:25]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 872388HCID 872388, compoundHCID 178506676HCID 178506676, compound

Product 1

HCID 68434734HCID 68434734, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In 10 ml of tetrahydrofuran is dissolved 2 g of N-[(1R)-1-(4-bromophenyl)ethyl]-2,2-dimethylpropanamide, and to this solution is dropwise added 14.3 ml of phenyllithium (1.48 M cyclohexane-diethyl ether solution), after which the temperature of the resulting mixture is elevated to −5° C. and the mixture is stirred at the same temperature for 4 hours. Subsequently, 1.06 g of paraformaldehyde is added thereto and the mixture is stirred at 5° C. for 1 hour, after which 6 ml of water is added to the reaction mixture and the organic layer is separated. The organic layer obtained is dried over anhydrous magnesium sulfate and the solvent is removed by distillation under reduced pressure. The residue obtained is purified by silica gel chromatography (eluant; n-hexane:ethyl acetate=2:1) to obtain 1.48 g (yield: 66.9%) of 5-bromo-2-{(1R)-1-[(2,2-dimethylpropanoyl)amino]-ethyl}benzyl alcohol.

Workup

  1. customis elevated to −5° C.
  2. stirringthe mixture is stirred at 5° C. for 1 hour
  3. customthe organic layer is separated
  4. customThe organic layer obtained
  5. dry with materialis dried over anhydrous magnesium sulfate
  6. customthe solvent is removed by distillation under reduced pressure
  7. customThe residue obtained
  8. customis purified by silica gel chromatography (eluant; n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record
ord-528286e9422b4311a8e77fc02a0655c2
Source dataset
uspto-grants-2008_05
Patent number
US07371868B2

Reaction notes

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