Sodium hydride → Ethyl 6''-chloro-4''-hydroxy-5,5-dimethyl-2''-oxo-dispiro[1,3-dioxane-2,1'-cyclohexane-4',1''-naphthalene]-3''-carboxylate

온도

0 °C

A stirred mixture of NaH (60% dispersion in mineral oil (0.39 mL, 9.3 mmol)) in 40 mL dioxane at room temperature, was treated with a mixture of (E)-benzaldehyde oxime (1.0 g, 8.6 mmol) in 40 mL DMF. The resulting mixture was stirred for 30 minutes. The mixture was then cooled to 0° C. and treated with a mixture of ethyl 4′-(4-chloro-2-(3-ethoxy-3-oxoprop-1-ynyl)phenyl)-5,5-dimethyl-spiro[1,3-dioxane-2,1′-cyclohexane]-4′-carboxylate (3.6 g, 7.8 mmol) in 30 mL DMF. The resulting mixture was stirred for 1 hour. The mixture was then carefully quenched with 10 mL H2O and brought to a pH of 5 by addition of 10% HCl. The mixture was extracted with ethyl ether (3×50 mL). The combined organic layers were washed with brine (20 mL), dried over anhydrous Na2SO4, concentrated in vacuo, and purified by column chromatography eluting with 20-30% EtOAc to give 2.2 g of the product as a pale yellow solid. MS (m/z)=435 (M+H)+.

1. stirringThe resulting mixture was stirred for 1 hour
2. customThe mixture was then carefully quenched with 10 mL H2O
3. additionbrought to a pH of 5 by addition of 10% HCl
4. extractionThe mixture was extracted with ethyl ether (3×50 mL)
5. washThe combined organic layers were washed with brine (20 mL)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated in vacuo
8. custompurified by column chromatography
9. washeluting with 20-30% EtOAc

ORD 기록

ord-8672b06c86ab4b828fb3eaffc7d34677

출처 데이터셋

uspto-grants-2009_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07635715B2