(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanol → HCID 59709037, compound

HRID 2423442Notes

Reaction equation

HRID 2423442 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[C:13]([CH2:14][OH:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[O:11][N:10]=1>ClCCl>[Cl:8][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=1[C:9]1[C:13]([CH:14]=[O:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[O:11][N:10]=1

Participants

3

Reactant 1

HCID 10850745(3-(2,6-Dichlorophenyl)-5-isopropylisoxazol-4-yl)methanol

Product 1

HCID 59709037HCID 59709037, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methanol (2.40 g, 8.39 mmol) in dichloromethane (160 mL) was added pyridinium chlorochromate-silica gel (20.2 wt %, 44.7 g, 41.9 mmol). The mixture was stirred for approximately 1.5 hours and then run through a silica gel pad and concentrated to afford 3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolecarbaldehyde (2.24 g, 7.88 mmol, 94%). 1H-NMR (400 MHz, DMSO-d6) δ 9.89 (s, 1H), 7.64-7.55 (m, 3H), 3.83 (septet, J=7 Hz, 1H), 1.39 (d, J=7 Hz, 6H).

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-0ee6401bd09c4f63ad249344ab415c8c
Source dataset
uspto-grants-2011_06
Patent number
US07960552B2

Reaction notes

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