Ammonium Chloride → HCID 131722969, compound

HRID 428206Notes

Reaction equation

HRID 428206 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:12]=1[O:13][CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[CH:8]=[O:9])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>C1COCC1>[CH3:19][Si:18]([CH3:21])([CH3:20])[C:17]#[C:16][C:10]1[C:11]([C:22]([CH3:25])([CH3:24])[CH3:23])=[C:12]([O:13][CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

4

Reactant 2

HCID 25517Ammonium ChlorideHCID 18357901HCID 18357901, compound

Product 1

HCID 131722969HCID 131722969, compoundYield 189%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

This solution is introduced dropwise into a solution of 15.4 g (42.3 mmol) of 3,5-di-tert-butyl-4-(2-trimethylsilylethoxymethoxy)benzaldehyde in 50 ml of THF at −78° C. The reaction medium is allowed to return to room temperature, poured into aqueous ammonium chloride solution and extracted with ethyl ether and the organic phase is separated out after settling has taken place, dried over magnesium sulphate and evaporated. 18.5 g (95%) of the expected alcohol are obtained in the form of a yellow oil.

Workup

  1. customto return to room temperature
  2. extractionextracted with ethyl ether
  3. customthe organic phase is separated out after settling
  4. dry with materialdried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-5405b4c8510345cf95d83c69e0efa4d5
Source dataset
uspto-grants-2001_11
Patent number
US06313162B1

Reaction notes

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