Hydrogen Peroxide → 5-fluoro-1-(hydroxymethyl)-2,3-dihydro-1H-indene-4-carbonitrile
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]2[C:7](=[CH2:11])[CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]#[N:13].B.C1C[O:18]CC1.[OH-].[Na+].OO>C1COCC1.O>[F:1][C:2]1[CH:10]=[CH:9][C:8]2[CH:7]([CH2:11][OH:18])[CH2:6][CH2:5][C:4]=2[C:3]=1[C:12]#[N:13]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 5-Fluoro-1-methylidene-2,3-dihydro-1H-indene-4-carbonitrile (30 mg, 0.173 mmol) in THF was added BH3.THF (0.173 ml, 0.173 mmol) at 0° C. The mixture was allowed to stir at 0° C. for 15 minutes, and then warm up to RT for 30 minutes. TLC showed little SM left at that point. To this reaction was then added Sodium Hydroxide (2M, 0.173 ml, 0.346 mmol) and Hydrogen peroxide (39.3 mg, 0.346 mmol). The mixture was stirred for another hour at RT. TLC and LC showed good reaction. The reaction was diluted with water, extracted with EtOAc, washed with water and brine, dried over Na2SO4, and concentrated. The resulting oil was used directly in the next step. LC-MS (IE, m/z): 192 [M+1]+.
Workup
- temperaturewarm up to RT for 30 minutes
- waitleft at that point
- stirringThe mixture was stirred for another hour at RT
- customreaction
- extractionextracted with EtOAc
- washwashed with water and brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-40d01cc91c254946ac1c82ad3e39822c
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09056859B2
Reaction notes
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