Benzaldehyde → HCID 13010486, compound

HRID 1640047Notes

Reaction equation

[CH3:1][C:2]([C:4]#[CH:5])=[CH2:3].[Li]CCCC.[CH:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH3:3][C:2](=[CH2:1])[C:4]#[C:5][CH:11]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:18]

Participants

Reactant 3

HCID 240Benzaldehyde

HCID 62323Isopropenylacetylene

HCID 178418339Butyllithium

Product 1

HCID 13010486HCID 13010486, compoundYield 93.9%

Procedure

2-Methylbut-1-en-3-yne (3.45 g, 52.19 mmol), nBuLi (36.0 mL, 57.6 mmol) and benzaldehyde (6.642 g, 62.63 mmol) were used according to the general method mentioned above. Purification of the resulting clear yellow-brown crude product yielded the pure product as a clear yellow-brown oil (8.442 g, 49.02 mmol, 93.9%): Rf 0.72 (hexanes/Et2O, 4:1); 1H NMR (300 MHz, CDCl3) δ 7.49-7.69 (m, 2H, H-8), 7.30-7.49 (m, 3H, H-9, 10), 5.58 (d, J=6.2 Hz, 1H, H-1), 5.37 (bs, 1H, H-5), 5.28 (p, J=1.5 Hz, 1H, H-5), 2.43 (d; J=6.2 Hz, 1H, —OH), 1.93 (bs, 3H, H-10); 13C NMR (300 MHz, CDCl3) δ 140.6 (C-7), 128.6 (C-9), 128.3 (C-10), 126.6 (C-8), 126.1 (C-4), 126.6 (C-5), 87.8 (C-2/3), 87.7 (C-2/3), 64.9 (C-1), 23.3 (C-6); HRMS calcd for C12H12O (M+) 172.0888. found 172.0885.

Workup

customPurification of the resulting clear yellow-brown crude product

Sources & evidence

ORD record: ord-5bdc5437a5e64e89a71c4c7578d31519
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08110695B2

Reaction notes

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