Acetone → HCID 10828369, compound

HRID 2257249Notes

Reaction equation

[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([C:16](=[O:18])[CH3:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[CH3:40][C:41]([CH3:43])=[O:42]>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([C:16](=[O:18])[CH2:17][C:41]([OH:42])([CH3:43])[CH3:40])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 1-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)-ethan-1-one (Example 2) (1.07 g, 4.3 mmol) in CH2Cl2 (65 mL) is cooled to -78° C., and diisopropylethylamine (0.97 mL, 5.6 mmol) and trimethylsilyltriflate (1.08 mL, 5.6 mmol) are added sequentially via syringe. The reaction is stirred at -78° C. for 10 min and then is allowed to warm to 24° C. and is stirred at that temperature for 45 min. The solution is once again cooled to -78° C., and acetone (0.54 mL, 4.3 mmol) is added, followed by TiCl4 (1M solution in CH2Cl2, 4.3 mL, 4.3 mmol). After 1 h at -78° C., the reaction mixture is allowed to warm to 24° C. and evaporated. The residue is partioned between MeOH/1N HCl and CH2Cl2. The CH2Cl2 layer is dried (MgSO4), filtered, evaporated, and chromatographed over SiO2 using EtOAc/hexane (1:6), to yield 1-(7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan-5-yl)-3-hydroxy-3-methylbutan-1-one.

Workup

temperatureto warm to 24° C.
stirringis stirred at that temperature for 45 min
temperatureThe solution is once again cooled to -78° C.
waitAfter 1 h at -78° C.
temperatureto warm to 24° C.
customevaporated
dry with materialThe CH2Cl2 layer is dried (MgSO4)
filtrationfiltered
customevaporated
customchromatographed over SiO2

Sources & evidence

ORD record: ord-125e0ef608214657b33dc7aa3dae04d9
Source dataset: uspto-grants-1997_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05656661

Reaction notes

Loading…