3,3-Dimethyl-1-butyne → HCID 68920489, compound

HRID 883744Notes

Reaction equation

HRID 883744 reaction equation
B(C1CCCCC1)C1CCCCC1.[CH3:14][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17].[Zn](CC)CC.[F:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1>>[F:25][C:26]1[CH:33]=[CH:32][C:29]([C@@H:30]([OH:31])[CH:17]=[CH:16][C:15]([CH3:19])([CH3:18])[CH3:14])=[CH:28][CH:27]=1

Participants

5

Reactant 4

HCID 135123,3-Dimethyl-1-butyneHCID 680234-FluorobenzaldehydeHCID 15879360CID 15879360HCID 178418750HCID 178418750, compound

Product 1

HCID 68920489HCID 68920489, compoundYield 82%

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 54 μL (0.50 mmol) p-fluorobenzaldehyde. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a white solid in 82% yield (85 mg, 0.41 mmol). m.p.: 38-40° C.; [α]D20=+21.3 (c=1.2, CHCl3, 93% ee); 1H NMR (CDCl3, 500 MHz): δ 1.01 (s, 9H), 1.84 (br s, 1H), 5.13 (d, 1H, J=6.9 Hz), 5.52 (dd, 1H, J=15.6, 6.9 Hz), 5.77 (d, 1H, J=15.6 Hz), 7.01 (t, 2H, J=8.7 Hz), and 7.31 (dd, 2H, J=8.3, 5.6 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz): δ 29.4, 32.9, 74.7, 115.1, 115.3, 127.1, 127.77, 127.83, 139.18, 139.20, 143.7, 161.1, and 163.1 ppm; IR (film): 3344, 3025, 2959, 2866, 1725, 1661, 1604, 1509, 1463, 1363, 1294, 1225, and 1156 cm−1; HRMS-CI m/z 208.1267 [M+; calcd for C13H17FO: 208.1263].

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-efa3287ea08440cabbdf2f014acc1e28
Source dataset
uspto-grants-2012_08
Patent number
US08236976B2

Reaction notes

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