Sodium hydride → HCID 131735581, compound

HRID 524362Notes

Reaction equation

[H-].[Na+].[Si:3]([O:20][CH2:21][C@H:22]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[NH:23]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:30][CH2:31][CH2:32][C:33]1[S:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=1>CN(C=O)C>[Si:3]([O:20][CH2:21][C@H:22]1[CH2:26][CH2:25][S:24](=[O:28])(=[O:27])[N:23]1[CH2:30][CH2:31][CH2:32][C:33]1[S:37][C:36]([C:38]([O:40][CH3:41])=[O:39])=[CH:35][CH:34]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a mixture of sodium hydride (37 mg, 1.54 mmol) in DMF (3.0 mL) cooled to 0° C. was added dioxide 8 (554 mg, 1.42 mmol). After 0.5 h a solution methyl 5-(3-iodopropyl)thiophene-2-carboxylate (485 mg, 1.56 mmol) in DMF (4.5 mL). The reaction was allowed to warm to room temperature on its own accord and stirred for 16 h. The reaction was quenched with saturated aqueous ammonium chloride and extracted with EtOAc. The organic portion was washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex) afforded 751 mg (91%) of ester 9.

Workup

temperatureto warm to room temperature on its own accord
customThe reaction was quenched with saturated aqueous ammonium chloride
extractionextracted with EtOAc
washThe organic portion was washed with brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customPurification of the residue by flash column chromatography (silica gel, 20% EtOAc/hex)

Sources & evidence

ORD record: ord-5615229e6e034aa0ba265a1ceaead14b
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09340534B2

Reaction notes

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