Methanol → HCID 22966592, compound

HRID 275755Notes

Reaction equation

HRID 275755 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 (DIBAL) 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 (MgSO4), 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 (MgSO4)
  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-627bae0bd0cc49209d36d05da942ec66
Source dataset
uspto-grants-2002_03
Patent number
US06353000B1

Reaction notes

Loading…