Acetic Acid → HCID 131727097, compound

HRID 16217Notes

Reaction equation

HRID 16217 reaction equation
[CH3:1][Si](C=[N+]=[N-])(C)C.[C:8]([SiH2:12][O:13][C:14]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH:15]([CH:22]=[CH2:23])[C:16]([CH3:21])([CH3:20])[C:17]([OH:19])=[O:18])([CH3:11])([CH3:10])[CH3:9].C(O)(=O)C>C1(C)C=CC=CC=1.CO>[CH3:1][O:18][C:17](=[O:19])[C:16]([CH3:21])([CH3:20])[CH:15]([C:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[O:13][SiH2:12][C:8]([CH3:9])([CH3:10])[CH3:11])[CH:22]=[CH2:23]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 167693TrimethylsilyldiazomethaneHCID 1317270983-(Tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-pent-4-enoic acid

Product 1

HCID 131727097HCID 131727097, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Trimethylsilyl diazomethane (29 mL, 2 M in hexanes, 57.78 mmol) was added to a stirred solution of Example 5G (15.58 g, 39.3 mmol) in toluene (100 mL) and methanol (20 mL). After one hour at room temperature, acetic acid (1.5 mL) was added to quench the excess reagent. The solvent was evaporated and the crude product was dissolved in diethyl ether and washed with NaHCO3 solution brine, dried (MgSO4), filtered, and evaporated. The title compound was isolated as an oil and used without further purification.

Workup

  1. customto quench the excess reagent
  2. customThe solvent was evaporated
  3. dissolutionthe crude product was dissolved in diethyl ether
  4. washwashed with NaHCO3 solution brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-bee3bea5d77d4ddb9c45b11e53dbd16a
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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