Sodium hydride → Ethyl 5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate

HRID 1868835Notes

Reaction equation

C(=N/[OH:9])\C1C=CC=CC=1.[H-].[Na+].[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([CH3:26])([CH3:25])[C:20]([O:22]CC)=O)[C:14]=1[C:27]#[C:28][C:29]([O:31][CH2:32][CH3:33])=[O:30]>CN(C=O)C.O1CCOCC1>[Cl:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]2[C:14]=1[C:27]([OH:9])=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:20](=[O:22])[C:19]2([CH3:25])[CH3:26]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of (E)-benzaldehyde oxime (234 mg, 1.93 mmol) in dry DMF (9 mL) was added to a suspension of NaH (46 mg, 1.93 mmol) in dioxane (9 mL) at room temperature. The mixture was stirred for 30 minutes and then cooled to 0° C. A solution of ethyl 3-(2-chloro-6-(1-ethoxy-2-methyl-1-oxopropan-2-yl)phenyl)propiolate (520 mg, 1.61 mmol) in dry DMF (9 mL) was added, and the mixture was stirred at 0° C. for 3 hours and then at room temperature for 1 hour. The mixture was quenched with water and then washed with EtOAc (2×). The aqueous layer was made acidic with 10% HCl and then extracted with EtOAc (2×). The extracts were dried over anhydrous MgSO4 and concentrated under vacuum. The residue was purified by flash chromatography to give 210 mg of ethyl 5-chloro-4-hydroxy-1,1-dimethyl-2-oxo-naphthalene-3-carboxylate as a colorless oil. MS m/e=295 (M+H)+.

Workup

stirringthe mixture was stirred at 0° C. for 3 hours
waitat room temperature for 1 hour
customThe mixture was quenched with water
washwashed with EtOAc (2×)
extractionextracted with EtOAc (2×)
dry with materialThe extracts were dried over anhydrous MgSO4
concentrationconcentrated under vacuum
customThe residue was purified by flash chromatography

Sources & evidence

ORD record: ord-c656532bef884bbab7598131d77a9ec9
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635715B2

Reaction notes

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