Propanal → HCID 86632043, compound

HRID 883748Notes

Reaction equation

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

Participants

Reactant 4

HCID 527Propanal

HCID 135123,3-Dimethyl-1-butyne

HCID 15879360CID 15879360

HCID 178418750HCID 178418750, compound

Product 1

HCID 86632043HCID 86632043, compoundYield 68%

Procedure

The product was prepared by General procedure S using 196 mg (1.1 mmol) Cy2BH, 137 μL (1.1 mmol) 3,3-dimethyl-1-butyne, 1.1 mL (2.1 mmol, 2.0 M in hexanes) Et2Zn, 9.6 mg (0.04 mmol) (−)-MIB, and 72 μL (1.0 mmol) propanal. The crude product was purified by column chromatography (5% ethyl acetate in hexanes) to afford the title compound as a colorless oil in 68% yield (96 mg, 0.68 mmol). [α]D20=−60.3 (c=0.63, CHCl3, 77% ee); 1H NMR (CDCl3, 500 MHz): δ 0.86 (t, 3H, J=7.4 Hz), 0.98 (s, 9H), 1.26 (br s, 1H), 1.44-1.59 (m, 2H), 3.93 (dt, 1H, J=6.6, 6.6 Hz), 5.31 (dd, 1H, J=15.7, 7.1 Hz), and 5.62 (d, 1H, J=15.7 Hz) ppm; 13C{1H} NMR (CDCl3, 125 MHz): δ 9.7, 22.6, 29.5, 30.2, 74.7, 127.4, and 143.2 ppm; IR (neat): 3360, 3025, 2960, 2866, 1660, 1478, 1463, 1414, 1384, 1363, 1331, and 1262 cm−1; HRMS-CI m/z 141.1274 [(M−H)+; calcd for C9H17O: 141.1279].

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-94b6599429784e47abf5a593390b02da
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236976B2

Reaction notes

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