Ammonia → HCID 15294443, compound

HRID 1737192Notes

Reaction equation

HRID 1737192 reaction equation
[Na].N.[OH:3][C:4]1[C:9]([CH3:10])=[CH:8][C:7]([CH:11]([CH2:13][Si:14]([CH3:17])([CH3:16])[CH3:15])O)=[CH:6][C:5]=1[CH3:18].C(OCC)C>C(O)C>[CH3:18][C:5]1[CH:6]=[C:7]([CH2:11][CH2:13][Si:14]([CH3:15])([CH3:17])[CH3:16])[CH:8]=[C:9]([CH3:10])[C:4]=1[OH:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 5360545SodiumHCID 15294442HCID 15294442, compound

Product 1

HCID 15294443HCID 15294443, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Mix sodium metal (520 mg, 22.6 mmol) and liquid ammonia (13 mL). To this solution add, by dropwise addition, a solution of 4-hydroxy-3,5-dimethyl-α-[(trimethylsilyl)-methyl]benzenemethanol (2.22 g, 10 mmol) in ethyl alcohol (O.5 g) and ethyl ether (5 ml). After the blue color disappears, cautiously add water (13 mL), extract with ethyl ether, dry (MgSO4), and evaporate the solvent. Purify the residue by silica gel chromatography to yield the title compound.

Workup

  1. additionTo this solution add, by dropwise addition
  2. extractioncautiously add water (13 mL), extract with ethyl ether
  3. dry with materialdry (MgSO4)
  4. customevaporate the solvent
  5. customPurify the residue by silica gel chromatography

Sources & evidence

ORD record
ord-27017e848b424aceaa52560c8b07e6c2
Source dataset
uspto-grants-1999_10
Patent number
US05962435

Reaction notes

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