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

HRID 30826Notes

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-392b758b65454008a57e864d7294e1ca
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423150B2

Reaction notes

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