Potassium Hydroxide → (S)-5-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-ol

HRID 593406Notes

Reaction equation

HRID 593406 reaction equation
[OH-].[K+].[C:3]1([CH2:9][CH2:10][C:11](=[O:24])[C:12]#[C:13][Si:14]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:15]([CH3:17])[CH3:16])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>CC1C=CC(C(C)C)=CC=1.CC1C=CC(S([N-][C@H]([C@@H](N)C2C=CC=CC=2)C2C=CC=CC=2)(=O)=O)=CC=1.Cl[Ru+].C(O)CC>[C:3]1([CH2:9][CH2:10][C@H:11]([OH:24])[C:12]#[C:13][Si:14]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:21]([CH3:22])[CH3:23])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 900322545-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-one

Product 1

HCID 90032808(S)-5-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-ol

Reagents, catalysts & solvents 2

HCID 11974997Chloridoruthenium(1+) [(1S,2S)-2-amino-1,2-diphenylethyl](4-methylbenzene-1-sulfonyl)azanide--1-methyl-4-(propan-2-yl)benzene (1/1/1)CatalystHCID 10311-PropanolSolvent

Procedure

Following a modified procedure of Trost (Trost, B. M. et al., J. Am. Chem. Soc. 128, 6745-6754 (2006)); Potassium hydroxide (8.5 mg, 0.15 mmol, 1.2 mol %) and RuCl(p-cymene)[(S,S)-Ts-DPEN] (80.7 mg, 0.127 mmol, 1 mol %) were added to) PrOH (110 ml) and the resultant mixture was stirred for 2 min at r.t. 5-Phenyl-1-(triisopropylsilyl)pent-1-yn-3-one 84 (4.0 g, 12.7 mmol, 1 eq.) was added via syringe and the mixture was stirred at r.t. for 45 min. The mixture was concentrated in vacuo to give the crude product. This was purified by column chromatography on silica, eluting with petrol/Et2O (20:1 to 10:1), giving the title product 85 as a clear, colourless oil (4.0 g, 99%). The enantiomeric excess was determined to be 99% via HPLC analysis of its derivative 87. Analytical data consistent with the literature (Trost, B. M. et al., J. Am. Chem. Soc. 128, 6745-6754 (2006)).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto give the crude product
  3. customThis was purified by column chromatography on silica
  4. washeluting with petrol/Et2O (20:1 to 10:1)

Sources & evidence

ORD record
ord-7d3f6702dcec485a92774ca78c2186ad
Source dataset
uspto-grants-2016_01
Patent number
US09242954B2

Reaction notes

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