3,3-Dimethyl-1-butyne → HCID 68918155, compound

HRID 883742Notes

Reaction equation

HRID 883742 reaction equation
B(C1CCCCC1)C1CCCCC1.[CH3:14][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17].[Zn](CC)CC.[Br:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=[O:29]>>[Br:25][C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[C@@H:28]([OH:29])[CH:17]=[CH:16][C:15]([CH3:19])([CH3:18])[CH3:14]

Participants

5

Reactant 4

HCID 135123,3-Dimethyl-1-butyneHCID 811292-BromobenzaldehydeHCID 15879360CID 15879360HCID 178418750HCID 178418750, compound

Product 1

HCID 68918155HCID 68918155, compoundYield 76%

Procedure

The product was prepared by General procedure S using 50 mg (0.28 mmol) Cy2BH, 35 μL (0.28 mmol) 3,3-dimethyl-1-butyne, 0.26 mL (0.53 mmol, 2.0 M in hexanes) Et2Zn, 2.4 mg (0.01 mmol) (−)-MIB, and 29 μL (0.25 mmol) o-bromobenzaldehyde. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 76% yield (51 mg, 0.19 mmol). [α]D20=−31.8 (c=0.33, CHCl3, 93% ee); 1H NMR (CDCl3, 500 MHz): δ 1.02 (s, 9H), 2.03 (s, 1H), 5.46-5.53 (m, 2H), 5.86 (d, 1H, J=15.0 Hz), 7.13 (t, 1H, J=7.6 Hz), 7.33 (t, 1H, J=7.5 Hz), 7.52 (d, 1H, J=8.9 Hz), and 7.54 (d, 1H, J=8.2 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz): δ 29.4, 33.0, 73.8, 122.6, 125.0, 127.7, 127.8, 128.9, 132.8, 142.3, and 144.3 ppm; IR (neat): 3353, 3064, 3013, 2958, 2865, 1721, 1661, 1590, 1568, 1465, 1439, 1363, and 1267 cm−1; HRMS-CI m/z 251.0432 [(M−OH)+; calcd for C13H16Br: 251.0435].

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-1c684603514f494dab1f5440fff3f3f4
Source dataset
uspto-grants-2012_08
Patent number
US08236976B2

Reaction notes

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