Ethyl Acetate → HCID 22951509, compound

HRID 275826Notes

Reaction equation

HRID 275826 reaction equation
[O:1]([C@@H:19]1[CH2:27][C@@H:22]2[O:23][C:24](=[O:26])[CH2:25][C@@H:21]2[C@H:20]1[CH2:28][CH2:29][C:30]1([O:43][CH2:42][CH2:41][O:40]1)[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=1)[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.CC(C[AlH]CC(C)C)C.C(OCC)(=O)C.C([O-])(=O)C(C(C([O-])=O)O)O.[K+].[Na+]>C1(C)C=CC=CC=1>[O:1]([C@@H:19]1[CH2:27][C@@H:22]2[O:23][CH:24]([OH:26])[CH2:25][C@@H:21]2[C@H:20]1[CH2:28][CH2:29][C:30]1([O:40][CH2:41][CH2:42][O:43]1)[CH2:31][O:32][C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([Cl:39])[CH:34]=1)[Si:2]([C:15]([CH3:16])([CH3:18])[CH3:17])([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

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 9855836Potassium sodium tartarateHCID 22951510HCID 22951510, compound

Product 1

HCID 22951509HCID 22951509, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 11 (945 mg, 1.55 mmol) in toluene (11 mL) at −78° C. (bath temperature) was added a 1.5 M solution of DIBAL-H in toluene (3.0 mL, 4.5 mmol). After 3.5 h, ethyl acetate (10 mL) was added, the mixture was warmed to room temperature, saturated sodium potassium tartarate (20 mL) was added, and the thick solution was stirred for 30 min to break the emulsion. The layers were separated, the aqueous phase was extracted with ethyl acetate (2×30 mL), the combined organic layers were dried (magnesium sulfate), filtered, concentrated, and chromatographed on a 13 cm tall×26 mm diameter silica gel column eluting with 40% ethyl acetate in hexane to afford 12 (968 mg, 100%).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (2×30 mL)
  3. dry with materialthe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customchromatographed on a 13 cm tall×26 mm diameter silica gel column
  7. washeluting with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1a955841d90d44868562e4cd108c00b3
Source dataset
uspto-grants-2002_03
Patent number
US06353014B1

Reaction notes

Loading…