Water → HCID 25140028, compound

HRID 1669120Notes

Reaction equation

[CH3:1][C:2]([O:4][C:5]([CH3:7])=[O:6])=O.[CH2:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH:9]1CCO.N1C=CC=CC=1.O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:5]([O:4][CH2:2][CH2:1][CH:9]1[CH2:8][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)(=[O:6])[CH3:7]

Participants

Conditions

Temperature: 20 °C

Procedure

Ac2O (47 mL, 505 mmol) in DCM (50 mL) was added over 1 h to a stirred solution of alcohol 149 (54.5 g, 337 mmol), pyridine (52 mL, 981 mmol) and DMAP (1.65 g, 13 mol) in DCM (400 mL) and the resulting solution was stirred at 20° C. for 16 h. H2O (200 mL) was added, and the mixture stirred for 1 h. The organic fraction was washed with aqueous HCl solution (1 M, 100 mL) and H2O (150 mL), dried and the solvent evaporated to give acetate 150 (68.4 g, 99%) as a pale brown oil: 1H NMR δ 7.16-7.19 (m, 2H, Harom), 7.09-7.14 (m, 2H, Harom), 4.16 (t, J=6.8 Hz, 2H, CH2O), 3.04-3.10 (m, 2H, CH2), 2.48-2.66 (m, 3H, CH2, CH), 2.05 (s, 3H, COCH3), 1.85 (q, J=6.8 Hz, 2H, CH2); 13C NMR δ 171.1, 143.0 (2), 126.2 (2), 124.4 (2), 63.5, 39.1 (2), 37.0, 34.3, 21.0. Anal calcd for C13H16O2: C, 76.4; H, 7.9. Found: C, 76.6; H, 7.9%.

Workup

stirringthe mixture stirred for 1 h
washThe organic fraction was washed with aqueous HCl solution (1 M, 100 mL) and H2O (150 mL)
customdried
customthe solvent evaporated

Sources & evidence

ORD record: ord-50edb88485844ac58992f5659c90fce3
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07989451B2

Reaction notes

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