Dichloromethane → HCID 68933064, compound

HRID 388750Notes

Reaction equation

HRID 388750 reaction equation
[Si:1]([O:8][C@H:9]1[C:14](=[CH2:15])[C@H:13]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:12]/[C:11](=[CH:25]\[C:26](OCC)=[O:27])/[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClCCl.[H-].C([Al+]CC(C)C)C(C)C>C1(C)C=CC=CC=1>[Si:1]([O:8][C@H:9]1[C:14](=[CH2:15])[C@H:13]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:19])[CH3:20])[CH2:12]/[C:11](=[CH:25]\[CH2:26][OH:27])/[CH2:10]1)([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 21225700DiisobutylaluminumhydrideHCID 131730229HCID 131730229, compound

Product 1

HCID 68933064HCID 68933064, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The compound of Example 16K (589 mg, 1.3 mmol) was dissolved in 20 mL of toluene and 10 mL of dichloromethane and cooled in a dry ice/acetone bath. Diisobutylaluminum hydride (1 M in hexanes, 5.8 mL, 5.8 mmol) was added dropwise. After 1 hour, the reaction was quenched by the addition of 20 mL of 20% aqueous sodium potassium tartrate. To this mixture was added 25 mL of water followed by 6 mL of 2 N HCl. The resulting mixture was extracted three times with dichloromethane. The combined extracts were washed with 10% aqueous NaCl, dried over MgSO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (70 mL of SiO2, elution with dichloromethane) afforded the titled compound (294 mg, 55%), contaminated with ˜20% of an olefin isomer.

Workup

  1. customthe reaction was quenched by the addition of 20 mL of 20% aqueous sodium potassium tartrate
  2. additionTo this mixture was added 25 mL of water
  3. extractionThe resulting mixture was extracted three times with dichloromethane
  4. washThe combined extracts were washed with 10% aqueous NaCl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification
  9. washby silica gel chromatography (70 mL of SiO2, elution with dichloromethane)

Sources & evidence

ORD record
ord-4086cb297b0148fe8d82a4255e03bc9f
Source dataset
uspto-grants-2013_02
Patent number
US08377913B2

Reaction notes

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