2-Nitropropane → 3-Methyl-3-nitro-1,1,1-trifluorobutan-2-ol

HRID 36879

Reaction equation

C(O[CH:4]([OH:9])[C:5]([F:8])([F:7])[F:6])C.[N+:10]([CH:13]([CH3:15])[CH3:14])([O-:12])=[O:11].C(=O)([O-])[O-].[K+].[K+]>O>[CH3:14][C:13]([N+:10]([O-:12])=[O:11])([CH3:15])[CH:4]([OH:9])[C:5]([F:6])([F:7])[F:8]

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of triflouroacetaldehyde ethyl hemiacetal (2.58 ml), 2-nitropropane (1.81 ml) and potassium carbonate (111 mg) is stirred at 65° C. (oil bath temperature) for 6 hours followed by 2.5 days at room temperature. The reaction mixture is diluted with water (100 ml) and extracted with methylene chloride (100 ml+5×50 ml). The combined organic layers are dried over sodium sulphate and the solvent is evaporated under reduced pressure. Purification of the liquid residue by flash chromatography on silica gel (eluant n-hexane/ethylacetate 85:15) affords 3-methyl-3-nitro-1,1,1-trifluorobutan-2-ol as an oil (2.005 g)

Workup

waitfollowed by 2.5 days at room temperature
extractionextracted with methylene chloride (100 ml+5×50 ml)
dry with materialThe combined organic layers are dried over sodium sulphate
customthe solvent is evaporated under reduced pressure
customPurification of the liquid residue by flash chromatography on silica gel (eluant n-hexane/ethylacetate 85:15)

Sources & evidence

ORD record: ord-dd1d05ae442b432398f97755dff0385d
Source dataset: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05418238

Linked notes

Loading…