Diisobutylaluminumhydride → HCID 22262935, compound

HRID 489725Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.C([O:13][C:14]([C:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([O:25][CH3:26])[CH:23]=2)[N:18]([S:27]([CH3:30])(=[O:29])=[O:28])[C:17]=1[CH3:31])=O)C>O1CCCC1>[CH3:30][S:27]([N:18]1[C:19]2[C:24](=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:16]([CH2:14][OH:13])=[C:17]1[CH3:31])(=[O:29])=[O:28]

Participants

Conditions

Temperature: -78 °C

Procedure

Diisobutylaluminum hydride (6 ml, 6 mmol, 1M in dichloromethane) was added slowly at −78° C. under N2 to a solution of 1-methanesulfonyl-5-methoxy-2-methyl-1H-indole-3-carboxylic acid ethyl ester (0.4 g, 1.29 mmol) in anhydrous tetrahydrofuran (10 ml). The reaction mixture was stirred at −78° C. for 1.5 hours and then kept at 4° C. for 16 hours. The reaction was quenched with water and stirred for 0.5 hour. The insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography over silica gel eluting with 50 to 70% ethyl acetate in hexane to give (1-methanesulfonyl-5-methoxy-2-methyl-1H-indol-3-yl)-methanol as a white solid, (0.26 g, 75.2%). 1H NMR (CDCl3) δ: 2.59 (s, 3H), 3.00 (s, 3H), 3.87 (s, 3H), 4.79 (bs, 2H), 6.91 (dd, 1H, J=9.1 Hz, 2.6 Hz), 7.11 (d, 1H, J=2.6 Hz), 7.89 (dd, 1H, J=9.1 Hz, 0.3 Hz).

Workup

waitkept at 4° C. for 16 hours
customThe reaction was quenched with water
stirringstirred for 0.5 hour
customThe insoluble material was removed by filtration
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by flash column chromatography over silica gel eluting with 50 to 70% ethyl acetate in hexane

Sources & evidence

ORD record: ord-913393a360e4439eaf7384c8e84c4fdd
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06979696B2

Reaction notes

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