Ethyl Acetate → HCID 68704568, compound

HRID 639202Notes

Reaction equation

C(NC(C)C)(C)C.[Li].[Cl:9][CH:10]1[CH2:19][CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:20][CH3:21])[CH:16]=2)[C:11]1=[O:22].[NH4+].[Cl-].[CH3:25][CH2:26][O:27][C:28]([CH3:30])=[O:29]>C1COCC1>[CH2:26]([O:27][C:28](=[O:29])[CH2:30][C:11]1([OH:22])[C:12]2[C:17](=[CH:16][C:15]([O:20][CH3:21])=[CH:14][CH:13]=2)[CH2:18][CH2:19][CH:10]1[Cl:9])[CH3:25]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of EtOAc (7.2 ml, 73.96 mmol) in THF (20 ml) is slowly added under an atmosphere of argon at −78° C. to a solution of lithium diisopropylamine (prepared from 10.5 ml of diisopropylamine (73.96 mmol) and 46.2 ml of 1.6 M n-BuLi in hexane (73.96 mmol)) in THF (20 ml). After stirring at −78° C. for 30 minutes, a solution of 2-chloro-6-methoxy-3,4-dihydro-2H-naphthalen-1-one (7.79 g, 36.98 mmol) in THF (20 ml) is slowly added during 30 minutes. The reaction mixture is stirred at −78° C. for 24 h. TLC analysis indicates complete conversion of starting material. The reaction mixture is diluted with EtOAc and poured into a sat aqueous solution of NH4Cl. The organic layer is separated and washed with brine. After drying over Na2SO4, the solvent is removed. Purification by FCC (hexane/EtOAc 920:80 to 880:120) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.22 (t, J=9 Hz, 3H), 2.33-2.41 (m, 2H), 2.80-3.12 (m, 4H); 3.12 (s, 1H), 3.78 (s, 3H), 4.12 (q, J=9 Hz, 2H), 5.01-5.04 (m, 1H), 6.60-6.62 (m, 1H), 6.78-6.82 (m, 1H), 7.52 (d. J=10 Hz, 1H).

Workup

stirringThe reaction mixture is stirred at −78° C. for 24 h
customThe organic layer is separated
washwashed with brine
dry with materialAfter drying over Na2SO4
customthe solvent is removed
customPurification by FCC (hexane/EtOAc 920:80 to 880:120)

Sources & evidence

ORD record: ord-d1cfeedad65f47f4aa4d173628d49796
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07691861B2

Reaction notes

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