Hexane → HCID 57556582, compound

HRID 899249Notes

Reaction equation

HRID 899249 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:19])=[C:13]([CH:18]=1)[C:14](OC)=[O:15])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.CCCCCC>ClCCl>[Si:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:19])=[C:13]([CH2:14][OH:15])[CH:18]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8058HexaneHCID 21225700DiisobutylaluminumhydrideHCID 57556453HCID 57556453, compound

Product 1

HCID 57556582HCID 57556582, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of methyl 5-{[tert-butyl(dimethyl)silyl]oxy}-2-methylbenzoate (step 2, 810 mg, 2.89 mmol) in dichloromethane (15 mL) was added a 0.95 M solution of diisobutylaluminum hydride in hexane (6.69 mL, 6.35 mmol) at −78° C. The mixture was stirred at −78° C. for 2 h. The reaction was quenched by addition of water (6.7 mL) at −78° C. The mixture was diluted with dichloromethane (50 mL) and hexane (50 mL), and the mixture was stirred at room temperature for 16 h. The mixture was dried over magnesium sulfate, concentrated to afford 724 mg (99%) of the title compound as a colorless oil:

Workup

  1. customThe reaction was quenched by addition of water (6.7 mL) at −78° C
  2. additionThe mixture was diluted with dichloromethane (50 mL) and hexane (50 mL)
  3. stirringthe mixture was stirred at room temperature for 16 h
  4. dry with materialThe mixture was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b3c4cf6a8db54425bf340b3205321335
Source dataset
uspto-grants-2008_04
Patent number
US07354925B2

Reaction notes

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