Triethylamine → HCID 22408124, compound

HRID 1654722Notes

Reaction equation

HRID 1654722 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[CH3:10].C(N(CC)CC)C.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])=[CH:4][C:3]=1[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 10987288(4-Bromo-3-methylphenyl)methanol

Product 1

HCID 22408124HCID 22408124, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromo-5-hydroxymethyltoluene (87.4 g) in methylene chloride (350 ml) were added, under ice-cooling with stirring, trietylamine (72.7 ml) and 4-dimethylaminopyridine (DMAP)(500 mg), and then thereto was added t-butyldimethylsilyl chloride (65.5 g). The mixture was stirred at 0° C. for 15 minutes, and stirred at room temperature for 3 hours. The reaction mixture is filtrated, and the filtrate was concentrated under reduced pressure. To the residure was added water (100 ml), and the mixture was extracted with ethyl acetate.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at 0° C. for 15 minutes
  3. stirringstirred at room temperature for 3 hours
  4. filtrationThe reaction mixture is filtrated
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionTo the residure was added water (100 ml)
  7. extractionthe mixture was extracted with ethyl acetate

Sources & evidence

ORD record
ord-8f4ed98111824442b9f209c90c3cb9eb
Source dataset
uspto-grants-1995_04
Patent number
US05409928

Reaction notes

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