4-Methylbenzaldehyde → HCID 68918140, compound

HRID 883745Notes

Reaction equation

HRID 883745 reaction equation
B(C1CCCCC1)C1CCCCC1.[CH3:14][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17].[Zn](CC)CC.[C:25]1([CH3:33])[CH:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27][CH:26]=1>>[CH3:14][C:15]([CH3:19])([CH3:18])[CH:16]=[CH:17][C@@H:31]([C:28]1[CH:29]=[CH:30][C:25]([CH3:33])=[CH:26][CH:27]=1)[OH:32]

Participants

5

Reactant 4

HCID 77254-MethylbenzaldehydeHCID 135123,3-Dimethyl-1-butyneHCID 15879360CID 15879360HCID 178418750HCID 178418750, compound

Product 1

HCID 68918140HCID 68918140, compoundYield 86%

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 59 μL (0.50 mmol) p-tolualdehyde. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a white solid in 86% yield (88 mg, 0.43 mmol). m.p.: 38-40° C.; [α]D20=+52.7 (c=0.97, CHCl3, 95% ee); 1H NMR (CDCl3, 500 MHz): δ 0.95 (s, 9H), 1.83 (br s, 1H), 2.26 (s, 3H), 5.03 (d, 1H, J=6.7 Hz), 5.47 (dd, 1H, J=15.6, 6.8 Hz), 5.70 (d, 1H, J=15.6 Hz), 7.07 (d, 2H, J=7.7 Hz), and 7.17 (d, 2H, J=7.9 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz): δ 21.1, 29.4, 32.8, 75.2, 126.1, 127.2, 128.1, 137.1, 140.6, and 143.2 ppm; IR (film): 3346, 3023, 2959, 2865, 2361, 2334, 1655, 1613, 1513, 1478, 1461, 1416, 1388, 1362, and 1268 cm−1; HRMS-CI m/z 204.1509 [M+; calcd for C14H20O: 204.1514].

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-5a9b956681204194bdacd68e5870a532
Source dataset
uspto-grants-2012_08
Patent number
US08236976B2

Reaction notes

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