Formaldehyde → [4-[1-(Tert-butyldimethylsilanyloxy)hexyl]phenyl]methanol

HRID 606545

Reaction equation

HRID 606545 reaction equation
C([Li])(C)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([CH:13]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:9][CH:8]=1.[CH2:27]=[O:28]>CCCCC.C1COCC1>[Si:20]([O:19][CH:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:27][OH:28])=[CH:8][CH:9]=1)[CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 57438973((1-(4-Bromophenyl)hexyl)oxy)(tert-butyl)dimethylsilaneHCID 178418306HCID 178418306, compound

Product 1

HCID 67046104[4-[1-(Tert-butyldimethylsilanyloxy)hexyl]phenyl]methanolYield 69%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyllithium (6.6 mL of a 1.7 M solution in pentane, 11.32 mmol) was added to a solution of the aryl bromide 7 (2.0 g, 5.39 mmol) in THF (22 mL) at −78° C. After 0.5 h paraformaldehyde (323 mg, 8.09 mmol) was added. The reaction was warmed to room temperature and stirred for 16 h. The reaction was quenched with saturated aqueous NH4Cl and extracted with EtOAc. The organic portion was dried (MgSO4), filtered and concentrated in vacuo. FCC (silica gel, 6:1 hex/EtOAc) yielded 1.2 g (69%) of the alcohol 8 as a clear, colorless oil.

Workup

  1. customThe reaction was quenched with saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-67fbe19536ed4065ad1c29c3c4d64a78
Source dataset
uspto-grants-2011_03
Patent number
US07915316B2

Linked notes

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