Sodium borohydride → 2-(2-Fluoro-5-nitrophenyl)-2-methylbutane-1,4-diol

HRID 1963744Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([CH3:17])([CH2:14][CH:15]=C)[CH:12]=[O:13].[BH4-].[Na+].ClCCl.C[OH:24]>[Cl-].[Na+].O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[C:11]([CH3:17])([CH2:14][CH2:15][OH:24])[CH2:12][OH:13]

Participants

Conditions

Temperature: -78 °C

Procedure

2-(2-fluoro-5-nitrophenyl)-2-methylpent-4-enal (1 eq) was dissolved in dichloromethane:methanol (3:1) and cooled to −78° C. Ozone was then bubbled through the solution until a blue color was noticed. Air was then passed through the solution followed by the addition of sodium borohydride (5 eq). Resulting solution was allowed to warm to room temperature and diluted with brine, extracted with dichloromethane. Organics were dried with sodium sulfate and concentrated to afford 2-(2-fluoro-5-nitrophenyl)-2-methylbutane-1,4-diol. The product was used in the next step with no further characterization.

Workup

customOzone was then bubbled through the solution until a blue color
temperatureto warm to room temperature
extractionextracted with dichloromethane
dry with materialOrganics were dried with sodium sulfate
concentrationconcentrated

Sources & evidence

ORD record: ord-1bb2932d743a4877998da67d64d1369d
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415382B2

Reaction notes

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