Ethyl Acetate → HCID 58013238, compound

HRID 1799453Notes

Reaction equation

HRID 1799453 reaction equation
[CH2:1]([O:8][C@:9]1([CH3:32])[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:12]([CH2:22][O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[O:11][C:10]1=[O:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:8][C@:9]1([CH3:32])[C@H:13]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C@@H:12]([CH2:22][O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[O:11][CH:10]1[OH:31])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 8857Ethyl AcetateHCID 57755415HCID 57755415, compound

Product 1

HCID 58013238HCID 58013238, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
-65 °C

Procedure

To a solution of (3R,4R,5R)-3,4-Bis(benzyloxy)-5-(benzyloxymethyl)-3-methyl-dihydrofuran-2(3H)-one (250 mmol) in toluene (625 mL) cooled to −70° C. was added dropwise a 1.5 M solution of Dibal in Toluene (250 mL, 375 mmol) at such a rate so that the reaction temperature does not go above −65° C. The reaction was further stirred at −65° C. for 15 mins (TLC analysis showed completion of reaction, 25% ethyl acetate in hexanes). The excess Dibal was destroyed by adding acetone (40 mL) to the reaction mixture while maintaining the temperature below −60° C. The reaction was diluted with cold 2.5 N HCl (300 mL), water (475 mL) and allowed to warm to 0° C. The reaction was extracted with ethyl acetate (625 mL). The organic layer was separated and washed with brine (500 mL), dried over MgSO4, filtered and the filtrate was concentrated in vacuum to dryness to furnish (3R,4R,5R)-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-3-methyl-tetrahydrofuran-2-ol (112 g) as an oil, which was used in the next step without further purification.

Workup

  1. customdoes not go above −65° C
  2. customThe excess Dibal was destroyed
  3. additionby adding acetone (40 mL) to the reaction mixture
  4. temperaturewhile maintaining the temperature below −60° C
  5. additionThe reaction was diluted with cold 2.5 N HCl (300 mL), water (475 mL)
  6. temperatureto warm to 0° C
  7. extractionThe reaction was extracted with ethyl acetate (625 mL)
  8. customThe organic layer was separated
  9. washwashed with brine (500 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationthe filtrate was concentrated in vacuum to dryness

Sources & evidence

ORD record
ord-eae7c1b6f3c1435b9ac337cee5769f92
Source dataset
uspto-grants-2013_01
Patent number
US08344132B2

Reaction notes

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