Diisobutylaluminum hydride → HCID 18386363, compound

HRID 2298231Notes

Reaction equation

HRID 2298231 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[C:9]([Br:11])[C:8]([O:12][C:13]2[CH:18]=[C:17]([CH:19]([CH3:21])[CH3:20])[C:16]([O:22][CH3:23])=[CH:15][C:14]=2[C:24](=[O:31])[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:7]([Br:32])[CH:6]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[Br:11][C:9]1[CH:10]=[C:5]([CH2:4][CH2:3][OH:2])[CH:6]=[C:7]([Br:32])[C:8]=1[O:12][C:13]1[CH:18]=[C:17]([CH:19]([CH3:20])[CH3:21])[C:16]([O:22][CH3:23])=[CH:15][C:14]=1[CH:24]([OH:31])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 9916184HCID 9916184, compound

Product 1

HCID 18386363HCID 18386363, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-(2-benzoyl-5-isopropyl-4-methoxy-phenoxy)-3,5-dibromo-phenyl)-acetic acid methyl ester (100 mg, 0.17 mmol) in THF under N2 atmosphere was added DIBAL (0.87 ml, 5 eq) dropwise at 0° C. The reaction was stirred at 0° C. for 15 minutes and allowed to reach room temperature and stirred for another 2 h. The mixture was poured into ice, and the aqueous phase extracted with EtOAc and the combined organic layers were dried over MgSO4 and concentrated. Purification on silica gave 2-(3,5-dibromo-4-(2-(hydroxy-phenyl-methyl)-5-isopropyl-4-methoxy-phenoxy)-phenyl)-ethanol as a solid (mg, %). 1H NMR (CD3COCD3): d

Workup

  1. customto reach room temperature
  2. stirringstirred for another 2 h
  3. additionThe mixture was poured into ice
  4. extractionthe aqueous phase extracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. concentrationconcentrated
  7. customPurification on silica

Sources & evidence

ORD record
ord-bd6ebdfbc1894ec781ccff8b31e82397
Source dataset
uspto-grants-2002_12
Patent number
US06492424B1

Reaction notes

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