Diisopropylamine → HCID 58264999, compound

HRID 2263634Notes

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[C:23]([C:32](Cl)=[O:33])=[CH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2>>[OH:21][C:22]1[C:23]([C:32](=[O:33])[CH2:14][C:13]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])=[CH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2

Participants

Reactant 4

HCID 7912Diisopropylamine

HCID 10908tert-Butyl acetate

HCID 128963863-Hydroxynaphthalene-2-carbonyl chloride

HCID 178418339Butyllithium

Product 1

HCID 58264999HCID 58264999, compound

Procedure

Prepared according to above procedure using diisopropylamine (2.0 mL, 15 mmol), nBuLi (11.4 mL, 1.2 M), tert-butyl acetate (3.4 mL, 12 mmol), 3-hydroxynaphthalene-2-carbonyl chloride (3.9 mmol, prepared from 730 mg of 3-hydroxy-2-naphthoic acid and SOCl2, 0.9 mL, heated to 40° C. in 9 mL toluene for 4 h) yielding 666 mg (57%) as yellow needles. mp=80-84° C.; IR (film) 2981.9; 2919.0; 1732.1; 1642.5; 1261.4; 1147.6 cm−1; 1H NMR (500 MHz, CDCl3) δ 11.17 (s, 1H); 8.29 (s, 1H); 7.78 (d, J=8.0 Hz, 1H); 7.65 (d, J=8.2 Hz, 1H); 7.50 (t, J=7.0, 1H); 7.33-7.27 (m, 2H); 4.05 (s, 2H); 1.42 (s, 9H); 13C NMR (125 MHz, CDCl3) δ 199.3, 166.2, 157.2, 138.5, 133.7, 130.2, 129.6, 127.1, 126.5, 124.5, 120.9, 112.7, 82.9, 47.8, 28.1; LRMS (electrospray): Mass calculated for C17H18O4, [M]+, 286.12. Found [M]+, 285.8.

Workup

customPrepared
customyielding 666 mg (57%) as yellow needles

Sources & evidence

ORD record: ord-819206bb80d7427d82c4c7e035a048ca
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07851640B2

Reaction notes

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