Ethyl 4-phenoxybenzoylformate → HCID 14329352, compound

HRID 1194771Notes

Reaction equation

HRID 1194771 reaction equation
CP([CH:5]1[S:10][CH2:9][S:8][CH2:7][S:6]1)(C)=O.C([Li])CCC.[O:16]([C:23]1[CH:28]=[CH:27][C:26]([C:29](=O)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[O:16]([C:23]1[CH:24]=[CH:25][C:26]([C:29](=[C:5]2[S:10][CH2:9][S:8][CH2:7][S:6]2)[C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:27][CH:28]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 2758881Ethyl 4-phenoxybenzoylformateHCID 15614287HCID 15614287, compoundHCID 178418339Butyllithium

Product 1

HCID 14329352HCID 14329352, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

In 50 ml of anhydrous tetrahydrofuran was dissolved 1.58 g of 2-dimethylphosphoryl-1,3,5-trithiane, and 4 ml of 1.6M n-butyl lithium was added dropwise under an argon atmosphere at a temperature of about -70° C. After completion of the dropwise addition, the resulting mixture was stirred for 1 hour. Next, a solution of 1.41 g of ethyl 4-phenoxyphenylglyoxylate dissolved in 5 ml of tetrahydrofuran was dropped thereinto. After completion of the dropping, the reaction temperature was slowly raised to room temperature and the mixture thus obtained was stirred overnight. Thereafter, the same treatment as in Example 1 was carried out to give a crude product, which was then purified by a silica gel column chromatography (chloroform:hexane=2:1) to obtain 1.63 g of the desired compound.

Workup

  1. additionwas added dropwise under an argon atmosphere at a temperature of about -70° C
  2. additionAfter completion of the dropwise addition
  3. additionwas dropped
  4. customthe mixture thus obtained
  5. stirringwas stirred overnight
  6. customto give a crude product, which
  7. customwas then purified by a silica gel column chromatography (chloroform:hexane=2:1)

Sources & evidence

ORD record
ord-52a2312a28a14b619a528179bf8d7d12
Source dataset
uspto-grants-1989_03
Patent number
US04816475

Reaction notes

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