Diisopropylamine → HCID 59595151, compound

HRID 2263633Notes

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].[OH:21][C:22]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:23]=1[C:24](Cl)=[O:25]>>[OH:21][C:22]1[CH:30]=[C:29]([CH3:31])[CH:28]=[CH:27][C:23]=1[C:24](=[O:25])[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 28776562HCID 28776562, compound

HCID 178418339Butyllithium

Product 1

HCID 59595151HCID 59595151, compound

Procedure

Prepared according to above procedure using diisopropylamine (3.8 mL, 28 mmol), nBuLi (21 mL, 1.2 M), tert-butyl acetate (2.1 mL, 16 mmol), 2-hydroxy-4-methylbenzoyl chloride (5 mmol, prepared from 760 mg 4-methyl-salicylic acid and SOCl2, 1.2 mL, heated to 47° C. in 12 mL toluene for 4 h) yielding 327 mg (26%) as white needles. mp=88-90° C.; IR (film) 1733.8; 1652.6; 1145.0 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.95 (s, 1H); 7.54 (d, J=8.2 Hz, 1H); 6.81 (s, 1H); 6.72 (d, J=8.2, 1H); 3.88 (s, 2H); 2.36 (s, 3H); 1.45 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 198.5, 166.5, 163.0, 148.9, 130.5, 120.7, 118.8, 117.2, 82.6, 47.4, 28.1, 22.2; LRMS (electrospray): Mass calculated for C14H18O4, [M]+, 250.12. Found [M+23]+, 272.9.

Workup

customPrepared
customyielding 327 mg (26%) as white needles

Sources & evidence

ORD record: ord-40b14117dc9a480782a6aaf0a4927cef
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851640B2

Reaction notes

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