3,3-Dimethyl-1-butyne → HCID 68917890, compound

HRID 883746Notes

Reaction equation

B(C1CCCCC1)C1CCCCC1.[CH3:14][C:15]([CH3:19])([CH3:18])[C:16]#[CH:17].[Zn](CC)CC.[CH:25]1([CH:31]=[O:32])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>>[CH:25]1([C@H:31]([OH:32])[CH:17]=[CH:16][C:15]([CH3:19])([CH3:18])[CH3:14])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

Reactant 4

HCID 135123,3-Dimethyl-1-butyne

HCID 16275Cyclohexanecarboxaldehyde

HCID 15879360CID 15879360

HCID 178418750HCID 178418750, compound

Product 1

HCID 68917890HCID 68917890, compoundYield 80%

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 61 μL (0.50 mmol) cyclohexane-carboxaldehyde. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 80% yield (78 mg, 0.40 mmol). [α]D20=−27.7 (c=0.13, CHCl3, 96% ee); 1H NMR (CDCl3, 500 MHz): δ 0.92-0.97 (m, 2H), 1.01 (s, 9H), 1.11-1.26 (m, 4H), 1.41 (m, 1H), 1.64 (m, 2H), 1.73 (m, 2H), 1.86 (br d, 1H, J=12.6 Hz), 3.75 (t, 1H, J=7.0 Hz), 5.35 (dd, 1H, J=15.6, 7.5 Hz), and 5.62 (d, 1H, J=15.7 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz): δ 26.1, 26.2, 26.6, 28.76, 28.84, 29.6, 32.9, 43.8, 77.9, 126.2, and 143.9 ppm; IR (neat): 3351, 2953, 2926, 2853, 1655, 1473, 1450, 1387, 1362, 1305, 1260, and 1204 cm−1; HRMS-CI m/z 195.1743 [(M−H)+; calcd for C13H23O: 195.1749].

Workup

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

Sources & evidence

ORD record: ord-6260ae7d986b4fe79effd7459c078d46
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236976B2

Reaction notes

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