Diisobutylaluminum hydride → HCID 66636327, compound

HRID 1093931Notes

Reaction equation

[CH3:1][C:2]1[C:3](=[O:28])[O:4][CH:5]([CH2:7][O:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:3]([OH:28])[O:4][CH:5]([CH2:7][O:8][C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 3-methyl-5-trityloxymethyl-5H-furan-2-one (1.85 g, 5 mmol, prepared by the method of Lopez-Herrera et. al., J. Carbohydrate Chem. 1994, 13, 767) in toluene (25 mL) under N2 atmosphere at −78° C. was added dropwise with stirring DiBAL (10 mL, 10 mmol, 1M solution in toluene). The addition rate was maintained to keep the temperature of the reaction below −70° C. The reaction was stirred at −78° C. for 2 h and quenched with ethyl acetate (4 mL) at that temperature. The reaction mixture was allowed to warm to room temperature and concentrated under vacuum to dryness. The residue obtained was purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexanes to furnish 1.65 g (88%) of 3-methyl-5-trityloxymethyl-2,5-dihydro-furan-2-ol (a mixture of isomers) as a white solid; mp 100-102° C.

Workup

temperatureThe addition rate was maintained
customthe temperature of the reaction below −70° C
customquenched with ethyl acetate (4 mL) at that temperature
temperatureto warm to room temperature
concentrationconcentrated under vacuum to dryness
customThe residue obtained
customwas purified by flash chromatography on silica gel eluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-d634df8cb0bc4607893679eea248ce88
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133870B2

Reaction notes

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