Ethanol → 2,2-Dicyclopropylethan-1-ol
Reaction equation
[CH:1]12B[CH:5]([CH2:6][CH2:7][CH2:8]1)[CH2:4][CH2:3]C2.[OH-].[Na+].[CH2:12]([OH:14])C.OO>O1CCCC1>[CH:7]1([CH:6]([CH:5]2[CH2:4][CH2:3]2)[CH2:12][OH:14])[CH2:8][CH2:1]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 5 °C
Procedure
To a solution of the compound of Preparation 155 (1 g, 9.24 mmol) in tetrahydrofuran (15 ml) under nitrogen was added 9-borabicyclo[3.3.1]nonane (18.5 ml of a 0.5M solution in tetrahydrofuran, 1 mol. equiv.) and the solution stirred for 18 hours. Sodium hydroxide (3.08 ml of a 3M aqueous solution, 1 mol. equiv.) was added followed by ethanol (5 ml). The reaction was cooled to 5° C. and hydrogen peroxide (3.14 ml of a 30% w/w aqueous solution, 3 mol. equiv.) added. The reaction was stirred at room temperature for 1 hour.
Workup
- additionequiv.) was added
- additionequiv.) added
- stirringThe reaction was stirred at room temperature for 1 hour
Sources & evidence
- ORD record
- ord-1582024c15674bbcada167b6b1251641
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05968923
Reaction notes
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