Ammonia → HCID 15294443, compound

HRID 1734295Notes

Reaction equation

HRID 1734295 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 (5ml). 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-7e29c42ccbbb458c875008d33f1a7416
Source dataset
uspto-grants-1996_07
Patent number
US05532400

Reaction notes

Loading…