Isobutyryl chloride → 1-(2,3-Dihydro-5-hydroxy-3,4,6-trimethyl-1H-indol-1-yl)-2,2-dimethyl-1-propanone

HRID 1488461Notes

Reaction equation

HRID 1488461 reaction equation
O[C:2]1C(C)=C2C(=CC=1C)NCC2C.[C:14]([N:19]1[C:27]2[C:22](=[C:23]([CH3:30])[C:24]([OH:29])=[C:25]([CH3:28])[CH:26]=2)[CH:21]([CH3:31])[CH2:20]1)(=[O:18])[CH:15]([CH3:17])[CH3:16].C(Cl)(=O)C(C)C>>[C:14]([N:19]1[C:27]2[C:22](=[C:23]([CH3:30])[C:24]([OH:29])=[C:25]([CH3:28])[CH:26]=2)[CH:21]([CH3:31])[CH2:20]1)(=[O:18])[C:15]([CH3:2])([CH3:17])[CH3:16]

Participants

4

Reactant 3

HCID 62325Isobutyryl chlorideHCID 22905634HCID 22905634, compoundHCID 22905653HCID 22905653, compound

Product 1

HCID 229056331-(2,3-Dihydro-5-hydroxy-3,4,6-trimethyl-1H-indol-1-yl)-2,2-dimethyl-1-propanoneYield 75%

Procedure

Treatment of indoline 10 (160 mg, 0.9 mmoI) according to a procedure similar to one used for preparing 11b, with substitution of pivaloyl chloride for isobutyryl chloride, afforded 11c (176 mg, 75% yield) as a colorless solid, mp 144°-145° C. Spectral data: 13C NMR: δ 11.7, 16.4, 19.5, 27.6, 39.9, 57.4, 117.9, 119.2, 121.9, 133.7, 136.0, 148.8, 176.0; HRMS: calcd. for C16H23NO2 261.1229, fnd. 261.1921. Anal: calcd. for C16H23NO2C, 73.53, H, 8.87, N, 5.36, fnd. C, 73.60, H, 8.91, N, 5.36.

Sources & evidence

ORD record
ord-2d090fb36c1f49e3b3b31169360d2c2c
Source dataset
uspto-grants-1997_10
Patent number
US05674876

Reaction notes

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