Tetrahydrofuran → HCID 67480396, compound

HRID 1915998Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[CH:6][C:5]=1[O:12][CH3:13].P(=O)([O-])OC(CC)(CC)[C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)NOC(C)(C)C)=[CH:21][CH:20]=1.[CH3:39][C:40]([CH3:43])([O-:42])[CH3:41].[K+].C([N:47]([CH2:50]C)CC)C.C1C[O:55]CC1>C(OCC)(=O)C>[CH3:1][O:2][CH:3]([O:14][CH3:15])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:25]/[C:22]2[CH:21]=[CH:20][C:19]([NH:47][C:50](=[O:55])[O:42][C:40]([CH3:43])([CH3:41])[CH3:39])=[CH:24][CH:23]=2)=[CH:6][C:5]=1[O:12][CH3:13]

Participants

Conditions

Temperature: 70 °C

Procedure

To a dry vial containing 4-formyl-2-methoxybenzaldehyde dimethylacetal (408 mg, 1.93 mmol) and diethyl-4-t-butoxycarbamoylbenzyl phosphonate (668 mg, 1 eq.) in THF (10 ml) was added potassium t-butoxide (265 mg, 1.2 eq.) in a glove box. The mixture was sealed under N2, heated to 70° C. and stirred at this temperature for 1 hr. To the cooled mixture was added triethylamine (0.5 ml), the crude product was diluted with ethyl acetate and adsorbed on silicagel. The product acetal was purified by MPLC using hexanes/ethyl acetate 10-60% gradient. MS (ESI+): 422 (M+23, M+Na+). Yield: 451.4 mg (66%).

Workup

customThe mixture was sealed under N2
customThe product acetal was purified by MPLC

Sources & evidence

ORD record: ord-e823c4a3411e4d8aa2ce7e4891852662
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08617515B2

Reaction notes

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