Potassium Carbonate → HCID 57971919, compound

HRID 1921888Notes

Reaction equation

HRID 1921888 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:28]=[C:29]([F:42])[C:30]=1[O:31][Si:32]([CH:39]([CH3:41])[CH3:40])([CH:36]([CH3:38])[CH3:37])[CH:33]([CH3:35])[CH3:34])[CH2:5][CH:6](/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[OH:27])[CH2:7][CH2:8][C:9]1[CH:18]=[CH:17][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:11][CH:10]=1.[C:43]([C:47]1[CH:54]=[CH:53][C:50]([CH2:51]Br)=[CH:49][CH:48]=1)([CH3:46])([CH3:45])[CH3:44].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:43]([C:47]1[CH:48]=[CH:49][C:50]([CH2:51][O:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2/[CH:20]=[CH:19]/[CH:6]([CH2:5][C:4]2[CH:28]=[C:29]([F:42])[C:30]([O:31][Si:32]([CH:36]([CH3:38])[CH3:37])([CH:39]([CH3:41])[CH3:40])[CH:33]([CH3:34])[CH3:35])=[C:2]([F:1])[CH:3]=2)[CH2:7][CH2:8][C:9]2[CH:10]=[CH:11][C:12]([C:13]([O:15][CH3:16])=[O:14])=[CH:17][CH:18]=2)=[CH:53][CH:54]=1)([CH3:46])([CH3:44])[CH3:45]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 878361-(Bromomethyl)-4-(1,1-dimethylethyl)benzeneHCID 57971924Methyl E-4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]-benzoate

Product 1

HCID 57971919HCID 57971919, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 1.3 g (2.19 mmol) of methyl E4-[3-(3,5-difluoro-4-triisopropylsilanyloxybenzyl)-5-(2-hydroxyphenyl)pent-4-enyl]benzoate in 20 ml of dry acetonitrile is mixed with 600 mg (2.62 mmol) of 4-tert-butylbenzyl bromide and 450 mg (3.28 mmol) of anhydrous potassium carbonate and heated under reflux for 12 hours. The mixture is then concentrated to dryness. The residue is taken up in ethyl acetate, washed with water and saturated sodium chloride solution, dried over sodium sulfate and concentrated. The resulting crude product is purified by preparative HPLC. 780 mg (48% of theory) of a colorless oil are obtained.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 12 hours
  3. concentrationThe mixture is then concentrated to dryness
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting crude product is purified by preparative HPLC
  8. custom780 mg (48% of theory) of a colorless oil are obtained

Sources & evidence

ORD record
ord-c49460fab9e647b9a5926ec9e26c0b0a
Source dataset
uspto-grants-2012_05
Patent number
US08173704B2

Reaction notes

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