Sodium borohydride → 1-Undecyn-3-ol, 1-(trimethylsilyl)-
Reaction equation
[CH3:1][Si:2]([CH3:16])([CH3:15])[C:3]#[C:4][C:5](=[O:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[BH4-].[Na+]>CO>[CH3:16][Si:2]([CH3:1])([CH3:15])[C:3]#[C:4][CH:5]([OH:14])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To 200 ml of methanol was added 10 g (41.93 mmol) of the product of Example 5. The reaction mixture was cooled to 0° C. and 0.53 g (14 mmol) of NaBH4 was added portionwise over 5 minutes. After an additional 15 minutes, the reaction was quenched with acetone and the solvent removed under reduced pressure. The residue was partitioned between water and diethyl ether. The aqueous layer was extracted one additional time with diethyl ether and the combined organic extracts were washed 1× with brine and then dried (MgSO4). Thin layer chromatography indicated the crude product to contain both the titled product and its unsilylated analogue. This was used in the next step without further purification.
Workup
- customthe reaction was quenched with acetone
- customthe solvent removed under reduced pressure
- customThe residue was partitioned between water and diethyl ether
- extractionThe aqueous layer was extracted one additional time with diethyl ether
- washthe combined organic extracts were washed 1× with brine
- dry with materialdried (MgSO4)
- customThis was used in the next step without further purification
Sources & evidence
- ORD record
- ord-f5c4c5cbc92e485aa776f996f1d33c11
- Source dataset
- uspto-grants-1990_11
- Patent number
- US04970234
Reaction notes
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