Hexane → Benzyl 3-(1-hydroxyethyl)-1H-indole-1-carboxylate

HRID 1381023Notes

Reaction equation

[Al].[Li].[C:3]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22](=[O:24])[CH3:23])=[CH:14]1)([O:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:4].CCCCCC>O1CCCC1.CCOCC>[C:3]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH:22]([OH:24])[CH3:23])=[CH:14]1)([O:5][CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[O:4]

Participants

Conditions

Temperature: -78 °C

Procedure

Lithium aluminum hydrode (1.2 g, 32 mmol) was suspended in tetrahydrofuran (100 ml) and cooled to -78° C. N-Carbobenzoxy-3-acetyl indole (19.3 g, 66 mmol) dissolved in tetrahydrofuran (200 ml) was added over 0.5 hr. and the reaction mixture was allowed to stir at -78° C. for 0.5 hr and then at 0° C. for 0.5 hr. Ether (300 ml) was added and the mixture was quenched with 1.2 ml H2O, 1.2 ml 2N NaOH, adn 3.6 ml and H2O. The mixture was filtered through celite, dried over MgSO4 and evaporated leaving a solid. The solid was dissolved in 50 ml hot ether and then hexane was added (300 ml). The resulting crystals were collected to afford 12.5 g (64% yield): mp 79°-80° C., which was identical with the material prepared above in procedure A.

Workup

additionwas added over 0.5 hr
waitat 0° C. for 0.5 hr
customthe mixture was quenched with 1.2 ml H2O, 1.2 ml 2N NaOH, adn 3.6 ml and H2O
filtrationThe mixture was filtered through celite
dry with materialdried over MgSO4
customevaporated
customleaving a solid
customThe resulting crystals were collected
customto afford 12.5 g (64% yield)
customprepared above in procedure A

Sources & evidence

ORD record: ord-20faff3311df4530bc020b812940f42b
Source dataset: uspto-grants-1986_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04584385

Reaction notes

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