Benzyl bromoacetate → HCID 68769595, compound

HRID 448194Notes

Reaction equation

HRID 448194 reaction equation
[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:15])[CH3:14])[CH:8]=1)=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].Br[CH2:32][C:33]([O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)=[O:34]>C1COCC1.CN1C(=O)N(C)CCC1.C(OCC)(=O)C>[CH3:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:16]([CH3:20])[C:3]=1[C:4]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13](=[O:15])[CH2:14][CH2:32][C:33]([O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[O:34])[CH:8]=1)=[O:5]

Participants

7

Reactant 3

HCID 62576Benzyl bromoacetateHCID 2733832Lithium HexamethyldisilazideHCID 68738533HCID 68738533, compound

Product 1

HCID 68769595HCID 68769595, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Conditions

Temperature
-65 °C

Procedure

To a stirred solution of 3-Acetylphenyl 2,6-dimethylbenzoate (Step B, 2.90 g, 10.8 mmol) in dry THF (50 ml) and DMPU (17 ml) was added a solution of lithium bis(trimethylsilyl) amide (1.0M, 11.89 ml) at −65° C. under argon. After 10 minutes of stirring at −65° C., benzyl bromoacetate (3.72 g, 16.24 mmol) was added rapidly. The reaction mixture was stirred for an additional 10 minutes and then warmed to room temperature for 4 hours. The crude mixture was taken in ethyl acetate and washed with water and brine. The aqueous layer was extracted one more time with ethyl acetate. The combined organic layers were dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hex: ethyl acetate, 4:1) to provide the title compound.

Workup

  1. stirringThe reaction mixture was stirred for an additional 10 minutes
  2. temperaturewarmed to room temperature for 4 hours
  3. washwashed with water and brine
  4. extractionThe aqueous layer was extracted one more time with ethyl acetate
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate, 4:1)

Sources & evidence

ORD record
ord-03224fd78dd9415c83c019b6039707eb
Source dataset
uspto-grants-2013_07
Patent number
US08481595B2

Reaction notes

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