Ethyl formate → HCID 67468834, compound

HRID 1908020Notes

Reaction equation

[H-].[Na+].[C:3]([C:7]1[CH:30]=[CH:29][C:10]([C:11]([N:13]2[CH2:18][CH2:17][C:16]3([CH2:27][C:26](=[O:28])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[O:19]3)[CH2:15][CH2:14]2)=[O:12])=[CH:9][C:8]=1[O:31][CH3:32])([CH3:6])([CH3:5])[CH3:4].[CH:33](OCC)=[O:34]>C1COCC1>[C:3]([C:7]1[CH:30]=[CH:29][C:10]([C:11]([N:13]2[CH2:14][CH2:15][C:16]3([C:27](=[CH:33][OH:34])[C:26](=[O:28])[C:25]4[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=4)[O:19]3)[CH2:17][CH2:18]2)=[O:12])=[CH:9][C:8]=1[O:31][CH3:32])([CH3:6])([CH3:4])[CH3:5]

Participants

Conditions

Temperature: 25 °C

Procedure

NaH (57 mg, 1.4 mmol) was added in small portions to a mixture of 1′-(4-tert-butyl-3-methoxy-benzoyl)spiro[chromane-2,4′-piperidine]-4-one (250 mg, 0.61 mmol) in THF (2.5 mL) at 25° C. A solution of ethyl formate (74 μL, 0.90 mmol) in THF (0.5 mL) was added and the mixture was allowed to stir at 25° C. for 3 h before it was quenched with 0.5M aqueous HCl. The layers were separated and the aqueous layer was extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over sodium sulfate, and concentrated in vacuo to provide 1′-(4-tert-butyl-3-methoxybenzoyl)-3-(hydroxymethylene)spiro[chroman-2,4′-piperidin]-4-one (50 mg, 19%) as an orange oil. ESI-MS m/z calc. 435.2. found 436.2 (M+1)+; Retention time: 1.87 minutes (3 min run).

Workup

customwas quenched with 0.5M aqueous HCl
customThe layers were separated
extractionthe aqueous layer was extracted with ethyl acetate (3×)
washThe combined organics were washed with brine
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5ed06386fe694323bc23fb4b2994098a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598164B2

Reaction notes

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