Iodoethane → methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)butanoate

HRID 1427258Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([N:13]2[C:21]3[C:16](=[C:17]([CH:22]=[O:23])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.I[CH2:35][CH3:36]>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:13]2[C:21]3[C:16](=[C:17]([CH:22]=[O:23])[CH:18]=[CH:19][CH:20]=3)[CH:15]=[CH:14]2)([CH2:35][CH3:36])[C:9]([O:11][CH3:12])=[O:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-(4-chlorophenyl)-2-(4-formyl-1H-indol-1-yl)acetate (2.34 g, 7.17 mmol) in THF (60 mL) and HMPA (15 mL) was added LiHMDS (1 M in THF, 11.0 mL, 11 mmol) dropwise at 0° C. The mixture was stirred at 0° C. for 30 min before adding iodoethane (1.23 g, 7.88 mmol). After stirring for another 30 min at 0° C., the mixture was diluted with EtOAc (120 mL) and then quenched with water (20 mL). The organic layer was separated and washed with brine (20 mL), dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was purified via column chromatography (0-15% EtOAc/hexanes) to provide the title compound.

Workup

stirringAfter stirring for another 30 min at 0° C.
customquenched with water (20 mL)
customThe organic layer was separated
washwashed with brine (20 mL)
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent was removed in vacuo
customThe residue was purified via column chromatography (0-15% EtOAc/hexanes)

Sources & evidence

ORD record: ord-509438ede45e4a1db05f0be18bd4973a
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933113B2

Reaction notes

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