Toluene → HCID 18443682, compound

HRID 459208Notes

Reaction equation

HRID 459208 reaction equation
C([O:8][C:9](=O)[C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1[Cl:24])C1C=CC=CC=1.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1>C1COCC1>[CH2:17]([O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[C:11]([Cl:24])[CH:12]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 22058608Benzyl 4-benzyloxy-2-chlorobenzoate

Product 1

HCID 18443682HCID 18443682, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-Benzyloxy-2 chloro-benzoic acid benzyl ester from Step A with DIBAL-H 1M in toluene (2.2 eq) in THF were stirred at room temperature for 3 hours. The quenched with tartrate saturated solution and extracted with ethyl acetate. Concentrated to dryness and purified by chromatography to afford the title compound.

Workup

  1. customThe quenched with tartrate saturated solution
  2. extractionextracted with ethyl acetate
  3. concentrationConcentrated to dryness
  4. custompurified by chromatography

Sources & evidence

ORD record
ord-579f7e2bb277405e8be4f5a0a8c92269
Source dataset
uspto-grants-2007_03
Patent number
US07192982B2

Reaction notes

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