Tetrahydrofuran → tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-formylvalerate

HRID 1912104Notes

Reaction equation

[Si:1]([O:18][CH2:19][CH2:20][CH:21]([C:30](=[O:35])NCOC)[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O1CCCC1.[H-].C([Al+]CC(C)C)C(C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(O)(=O)C>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([CH:30]=[O:35])[CH2:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])([C:14]([CH3:15])([CH3:17])[CH3:16])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

tert-Butyl 5-(tert-butyldiphenylsilanyloxy)-3-methoxymethylcarbamoylvalerate (4.61 g) and tetrahydrofuran (60 mL) were mixed. To the mixture was added dropwise diisobutylaluminum hydride (1.0 M in toluene) (13.1 mL) at −78° C. The mixture was stirred at −78° C. for 1.5 hr. To the mixture was added dropwise acetic acid (0.515 mL). After an addition of aqueous Rochelle salt at −20° C., the mixture was extracted with ethyl acetate. The organic layer washed with water, then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo. The resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/25) to give the title compound (2.60 g).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer washed with water
dry with materialdried over magnesium sulfate
filtrationThe magnesium sulfate was filtered off
concentrationthe filtrate was concentrated in vacuo
customThe resultant residue was purified by silica gel column chromatography (Eluent: ethyl acetate/hexane=1/25)

Sources & evidence

ORD record: ord-d4fcddd7217f4f609f18389659ed9d23
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08604069B2

Reaction notes

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