Ethyl Acetate → HCID 57856997, compound

HRID 561741Notes

Reaction equation

HRID 561741 reaction equation
[S:1]1[C:5]([C@H:6]([O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)/[CH:7]=[CH:8]/[C@@H:9]2[C@@H:16]3[C@@H:12]([O:13][C:14](=[O:17])[CH2:15]3)[CH2:11][C@H:10]2[OH:18])=[CH:4][C:3]2[CH:37]=[CH:38][CH:39]=[CH:40][C:2]1=2.CC(C[AlH]CC(C)C)C.C(OCC)(=O)C>C1COCC1>[S:1]1[C:5]([C@H:6]([O:19][Si:20]([C:33]([CH3:36])([CH3:35])[CH3:34])([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)/[CH:7]=[CH:8]/[C@@H:9]2[C@@H:16]3[C@@H:12]([O:13][CH:14]([OH:17])[CH2:15]3)[CH2:11][C@H:10]2[OH:18])=[CH:4][C:3]2[CH:37]=[CH:38][CH:39]=[CH:40][C:2]1=2

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14487Diisobutylaluminum hydrideHCID 57857063HCID 57857063, compound

Product 1

HCID 57856997HCID 57856997, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

(3aR,4R,5R,6aS)-4-((R,E)-3-(Benzo[b]thiophen-2-yl)-3-(tert-butyldiphenylsilyloxy)prop-1-enyl)-5-hydroxyhexahydro-2H-cyclopenta[b]furan-2-one (7a, limiting reagent) is dissolved in anhydrous THF (0.5 M) under a nitrogen atmosphere and cooled to −78° C. A solution consisting of DIBAL-H (1 M in toluene, 2 molar equivalents) is added to the reaction mixture dropwise and stirred for 3 hours. Ethyl acetate (20 mL) is added and the mixture is stirred for an additional 5 minutes. The mixture is then treated with 30% aqueous K, Na tartrate and stirred vigorously overnight. The layers are separated and the organic phase is filtered and concentrated under reduced pressure. The crude product is purified by flash chromatography on regular silica gel eluted with hexanes-ethyl acetate to afford the title intermediate 8a.

Workup

  1. additionis added to the reaction mixture dropwise
  2. stirringthe mixture is stirred for an additional 5 minutes
  3. stirringstirred vigorously overnight
  4. customThe layers are separated
  5. filtrationthe organic phase is filtered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product is purified by flash chromatography on regular silica gel
  8. washeluted with hexanes-ethyl acetate

Sources & evidence

ORD record
ord-3f3bdcf6b2bc46f8864099259509dc13
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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