Methanol → HCID 10583084, compound

HRID 1474749Notes

Reaction equation

HRID 1474749 reaction equation
[CH3:1][C:2]1([CH3:11])[O:10][C@@H:9]2[C@@H:4]([CH2:5][O:6][C:7]2=[O:8])[O:3]1.[H-].C([NH2+]CC(C)C)C(C)C.CO>C1(C)C=CC=CC=1>[CH3:1][C:2]1([CH3:11])[O:3][C@@H:4]2[CH2:5][O:6][C@@H:7]([OH:8])[C@@H:9]2[O:10]1

Participants

5

Reactant 3

HCID 887MethanolHCID 3868432,3-O-Isopropylidene-D-erythronolactoneHCID 21898182Diisobutylammonium hydride

Product 1

HCID 10583084HCID 10583084, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-O-isopropylidene-D-erythronolactone (1.04 g, 6.42 mmol) was dissolved in toluene (20 ml), followed by the addition of 1 M diisobutylammonium hydride (DIBAL)/THF to the solution at −78° C. The reaction mixture was stirred at the same temperature for 30 min and methanol was slowly added until the reaction terminated. The suspension was filtered through a Celite filter and the filtrate was extracted with ethyl acetate and water, followed by silica gel column chromatography using a mixture of hexane:ethylacetate (3:1, v/v) to give the object compound in syrup form (1.94 g, 96%).

Workup

  1. customterminated
  2. filtrationThe suspension was filtered through a Celite
  3. filtrationfilter
  4. extractionthe filtrate was extracted with ethyl acetate and water
  5. additiona mixture of hexane:ethylacetate (3:1
  6. customv/v) to give the object compound in syrup form (1.94 g, 96%)

Sources & evidence

ORD record
ord-3d528d8f367f484486e1ab4775b049c8
Source dataset
uspto-grants-2015_04
Patent number
US09018371B2

Reaction notes

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