Ammonia → HCID 15294443, compound

HRID 466305Notes

Reaction equation

HRID 466305 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(O)C.C(OCC)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 3

HCID 222AmmoniaHCID 5360545SodiumHCID 15294442HCID 15294442, compound

Product 1

HCID 15294443HCID 15294443, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

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 (0.5 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-dd31e188c733447fa9207fb416258414
Source dataset
uspto-grants-1992_10
Patent number
US05155250

Reaction notes

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