Diisopropylamine → HCID 57912472, compound

HRID 2263632Notes

Reaction equation

C(NC(C)C)(C)C.[Li]CCCC.[C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH3:14].[CH3:21][O:22][C:23]1[CH:24]=[C:25]([OH:33])[C:26](=[CH:31][CH:32]=1)[C:27](OC)=[O:28]>>[OH:33][C:25]1[CH:24]=[C:23]([O:22][CH3:21])[CH:32]=[CH:31][C:26]=1[C:27](=[O:28])[CH2:14][C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

Reactant 4

HCID 7912Diisopropylamine

HCID 10908tert-Butyl acetate

HCID 79523Methyl 4-methoxysalicylate

HCID 178418339Butyllithium

Product 1

HCID 57912472HCID 57912472, compound

Procedure

Prepared according to above procedure using diisopropylamine (8.0 mL, 58 mmol), nBuLi (34 mL, 1.6 M), tert-butyl acetate (4.7 mL, 35 mmol), methyl 4-methoxysalicylate (1.83 g, 10 mmol) yielding 2.04 g (76%) as white needles. mp=40-42° C.; IR (film) 2978.7; 2936.4; 1731.9; 1633.5; 1357.0; 1129.3 cm−1; 1H NMR (500 MHz, CDCl3) δ 12.42 (s, 1H); 7.57 (d, J=9.0 Hz, 1H); 6.45 (d, J=9.0, 1H); 6.44 (s, 1H); 3.85 (s, 3H); 3.84 (s, 2H); 1.46 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 197.1, 166.7, 166.6, 165.9, 132.3, 113.5, 108.3, 101.2, 82.5, 55.9, 47.2, 28.2; LRMS (electrospray): Mass calculated for C14H18O5, [M]+, 266.12. Found [M+23]+, 289.5.

Workup

customPrepared
customyielding 2.04 g (76%) as white needles

Sources & evidence

ORD record: ord-f9820e6399164a06834c4996f64d0346
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851640B2

Reaction notes

Loading…