3,3-Dimethyl-1-butyne → HCID 68922027, compound

HRID 883743Notes

Reaction equation

HRID 883743 reaction equation
B(C1CCCCC1)C1CCCCC1.[CH3:14][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17].[Zn](CC)CC.[F:25][C:26]([F:36])([F:35])[C:27]1[CH:34]=[CH:33][C:30]([CH:31]=[O:32])=[CH:29][CH:28]=1>>[CH3:14][C:15]([CH3:19])([CH3:18])[CH:16]=[CH:17][C@@H:31]([C:30]1[CH:29]=[CH:28][C:27]([C:26]([F:25])([F:35])[F:36])=[CH:34][CH:33]=1)[OH:32]

Participants

5

Reactant 4

HCID 135123,3-Dimethyl-1-butyneHCID 679964-(Trifluoromethyl)benzaldehydeHCID 15879360CID 15879360HCID 178418750HCID 178418750, compound

Product 1

HCID 68922027HCID 68922027, compoundYield 89%

Procedure

The product was prepared by General procedure S using 98 mg (0.55 mmol) Cy2BH, 68 μL (0.55 mmol) 3,3-dimethyl-1-butyne, 0.55 mL (1.1 mmol, 2.0 M in hexanes) Et2Zn, 4.8 mg (0.02 mmol) (−)-MIB, and 68 μL (0.50 mmol) p-trifluoromethylbenzaldehyde. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a white solid in 89% yield (115 mg, 0.45 mmol). m.p.: 30-32° C.; [α]D20=−10.0 (c=0.27, CHCl3, 95% ee); 1H NMR (CDCl3, 500 MHz): δ 0.98 (s, 9H), 2.03 (br s, 1H), 5.15 (d, 1H, J=7.0 Hz), 5.47 (dd, 1H, J=15.5, 7.2 Hz), 5.78 (d, 1H, J=15.6 Hz), 7.43 (d, 2H, J=8.0 Hz), and 7.55 (d, 2H, J=8.0 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz): δ 29.3, 33.0, 74.9, 123.1, 125.28, 125.31, 125.34, 126.4, 126.7, 129.4, 129.7, 144.6, and 147.3 ppm; IR (film): 3335, 3025, 2962, 2905, 2868, 1661, 162.0, 1477, 1463, 1414, 1364, and 1327 cm−1; HRMS-CI m/z 239.1247 [(M−F)+; calcd for C14H17F2O: 239.1247].

Workup

  1. customThe product was prepared by General procedure S
  2. customThe crude product was purified by column chromatography (5% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6b78e254198f4ddc8faafb06d41292a0
Source dataset
uspto-grants-2012_08
Patent number
US08236976B2

Reaction notes

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