Methanol → HCID 22966592, compound

HRID 480218Notes

Reaction equation

HRID 480218 reaction equation
[O:1]([CH2:19][C@H:20]1[C@@H:27]2[C@@H:23]([O:24][C:25](=[O:28])[CH2:26]2)[CH2:22][C@@H:21]1[F:29])[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H-].C([Al+]CC(C)C)C(C)C.CO.C([O-])(=O)C(C(C([O-])=O)O)O.[K+].[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[O:1]([CH2:19][C@H:20]1[C@@H:27]2[C@@H:23]([O:24][CH:25]([OH:28])[CH2:26]2)[CH2:22][C@@H:21]1[F:29])[Si:2]([C:15]([CH3:16])([CH3:17])[CH3:18])([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 22951117HCID 22951117, compound

Product 1

HCID 22966592HCID 22966592, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5 (989 mg, 2.40 mmol) in toluene (15 mL) at −78° C. (bath temperature) was added dropwise a 1.5 M solution of diisobutylaluminum hydride in toluene (2.4 mL, 3.6 mmol). After 1 h, methanol (2 mL) and ethyl acetate (2 mL) were added, the solution was warmed to room temperature, added to saturated sodium potassium tartarate (30 mL), and stirred for 30 min. The layers were separated, the aqueous phase was extracted with ethyl acetate (3×30 mL), dried (magnesium sulfate), filtered, concentrated, and chromatographed on a 10 cm tall×26 mm diameter silica gel column eluting with 40% ethyl acetate in hexane to afford 6 (832 mg, 84%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×30 mL)
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on a 10 cm tall×26 mm diameter silica gel column
  7. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-93ca0cd707d5439db7d645ffb42238f4
Source dataset
uspto-grants-2003_11
Patent number
US06649655B2

Reaction notes

Loading…