Methyl iodide → Methyl 2-(3-(3-(diphenyl(2-methyl-2-propyl)siloxy)phenyl)-3-hydroxypropyl)benzoat

HRID 258479Notes

Reaction equation

HRID 258479 reaction equation
[C:1]1([Si:7]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:28]([CH3:31])([CH3:30])[CH3:29])[O:8][C:9]2[CH:10]=[C:11]([CH:15]([OH:27])[CH2:16][CH2:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20]([OH:22])=[O:21])[CH:12]=[CH:13][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:38]([O-])([O-])=O.[K+].[K+].CI.CCOC(C)=O>CC(C)=O>[C:32]1([Si:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)([C:28]([CH3:30])([CH3:31])[CH3:29])[O:8][C:9]2[CH:10]=[C:11]([CH:15]([OH:27])[CH2:16][CH2:17][C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20]([O:22][CH3:38])=[O:21])[CH:12]=[CH:13][CH:14]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 197679292-(3-(3-(Diphenyl(2-methyl-2-propyl)siloxy)phenyl)-3-hydroxypropyl) benzoic acid

Product 1

HCID 19737267Methyl 2-(3-(3-(diphenyl(2-methyl-2-propyl)siloxy)phenyl)-3-hydroxypropyl)benzoatYield 98%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To the product of Example 2, Step 1 (95 g, 0.187 mol) in acetone (1 L) was added K2CO3 (55 g, 0.374 mol) and MeI (128 mL, 1.31 mol). After refluxing for 1.5 h, the reaction mixture was cooled to r.t. EtOAc (1 L) was then added to the reaction mixture and the K2CO3 was removed by filtration. The filtrate was evaporated to dryness to provide 93 g (98%) of the title ester.

Workup

  1. temperatureAfter refluxing for 1.5 h
  2. customthe K2CO3 was removed by filtration
  3. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-d0442d5d7b9440f3b6a796d1da595072
Source dataset
uspto-grants-1993_11
Patent number
US05266568

Reaction notes

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