Ammonia → HCID 15294443, compound

HRID 1488932Notes

Reaction equation

HRID 1488932 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-a3480d4c26fd400696ef9c8b07128090
Source dataset
uspto-grants-1997_10
Patent number
US05677291

Reaction notes

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