Pivalaldehyde → HCID 22606921, compound

HRID 2307590Notes

Reaction equation

HRID 2307590 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24](Br)=[CH:23][C:22]=2[CH3:28])[CH:18]=[CH:19][CH:20]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:46][C:47]([CH3:51])([CH3:50])[CH:48]=[O:49]>C1COCC1>[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=1[CH2:32][O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:13][O:14][C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24]([CH:48]([OH:49])[C:47]([CH3:51])([CH3:50])[CH3:46])=[CH:23][C:22]=2[CH3:28])[CH:18]=[CH:19][CH:20]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 12417PivalaldehydeHCID 22606902HCID 22606902, compoundHCID 178418339Butyllithium

Product 1

HCID 22606921HCID 22606921, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2 g (3 mmol) of 3′-[3,4-bis-(tert-butyldimethylsilanyloxymethyl)benzyloxy]-4-bromo-2-methylbiphenyl are dissolved in 30 mL of anhydrous THF and the mixture is cooled to −78° C. 1.4 mL (3.5 mmol) of 2.5 M butyllithium are added slowly and the mixture is maintained at −78° C. for 1 hour. 400 mL (3.7 mmol) of 2,2-dimethylpropionaldehyde are added dropwise and the medium is warmed slowly to room temperature and then treated according to the usual treatment. The desired product is obtained in the form of a colourless oil (m=2 g; Y=100%).

Workup

  1. temperaturethe mixture is maintained at −78° C. for 1 hour
  2. temperaturethe medium is warmed slowly to room temperature
  3. additiontreated

Sources & evidence

ORD record
ord-812d4fb78d96496fb6145efaf39ff00c
Source dataset
uspto-grants-2004_12
Patent number
US06831106B1

Reaction notes

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