Diisobutylaluminum hydride → HCID 58494021, compound

HRID 1942681Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5]([C:13]2[S:14][C:15]([C:18]3[C:19]([CH2:31][CH3:32])=[C:20]([CH2:24][CH2:25][C:26](OCC)=[O:27])[CH:21]=[CH:22][CH:23]=3)=[CH:16][N:17]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH:10]([CH3:12])[CH3:11])#[N:2].CC(C[AlH]CC(C)C)C>ClCCl>[CH2:31]([C:19]1[C:20]([CH2:24][CH2:25][CH:26]=[O:27])=[CH:21][CH:22]=[CH:23][C:18]=1[C:15]1[S:14][C:13]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH:10]([CH3:11])[CH3:12])=[C:3]([CH:4]=2)[C:1]#[N:2])=[N:17][CH:16]=1)[CH3:32]

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of ethyl 3-[3-(2-{3-cyano-4-[(1-methylethyl)oxy]phenyl}-1,3-thiazol-5-yl)-2-ethylphenyl]propanoate (D114) (900 mg, 2.006 mmol) in Dichloromethane (DCM) (20 mL) stirred under nitrogen at −70° C. was added a solution of DIBAL-H (4 ml, 4.00 mmol) dropwise during 30 min. The reaction mixture was stirred at −70° C. for 20 minutes. The reaction mixture was quenched with cooled aqueous HCl solution (10 mL, 10%). The organic layers were washed with water twice. Then the organic layers were separated and dried over anhydrous sodium sulphate. The organic solvent was evaporated in vacuo to afford 5-{5-[2-ethyl-3-(3-oxopropyl)phenyl]-1,3-thiazol-2-yl}-2-[(1-methylethyl)oxy]benzonitrile (D115) (1 g), which was used directly without further purification. MS (ES): C24H24N2O2S requires 404.2. found 405.2 (M+H+).

Workup

customThe reaction mixture was quenched with cooled aqueous HCl solution (10 mL, 10%)
washThe organic layers were washed with water twice
customThen the organic layers were separated
dry with materialdried over anhydrous sodium sulphate
customThe organic solvent was evaporated in vacuo

Sources & evidence

ORD record: ord-5a2baada49ba4f999a174602303f70f5
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08389508B2

Reaction notes

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