Ethyl Acetate → HCID 118307026, compound

HRID 921190Notes

Reaction equation

[F:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([O:12][CH:13]([CH2:18][CH:19]=[CH2:20])[C:14]([F:17])([F:16])[F:15])[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(OCC)(=O)C.C([O-])(O)=O.[Na+]>C1COCC1>[F:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[C:4]([O:12][CH:13]([CH2:18][CH:19]=[CH2:20])[C:14]([F:15])([F:16])[F:17])[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Methyl 4-fluoro-2-[(1,1,1-trifluoropent-4-en-2-yl)oxy]benzoate (2.92 g, 10 mmol) was dissolved in 20 mL of THF and cooled to 0° C. 1M (THF) LiAlH4 (10 mL, 10 mmol) was added and the mixture stirred for 3 hours. Ethyl acetate (10 mL) was added and the mixture stirred 5 min, after which sat'd NaHCO3 was added and stirring continued for 15 min. The mixture was transferred to a separatory funnel and extracted with ethylacetate. The organic layers were combined and dried over Na2SO4, filtered and the solvent removed under vacuum. The crude product was purified by column chromatography on a Biotage instrument using hexanes/ethyl acetate as eluent. 1H NMR (400 MHz, CDCl3) δ 2.70 (m, 2H), 4.64 (overlapping m, 3H), 5.23 (d, 1H), 5.27 (d, 1H), 5.84 (m, 1H), 6.68 (dd, 1H), 6.77 (td, 1H), 7.35 (m, 1H).

Workup

stirringthe mixture stirred 5 min
additionwas added
stirringstirring
waitcontinued for 15 min
customThe mixture was transferred to a separatory funnel
extractionextracted with ethylacetate
dry with materialdried over Na2SO4
filtrationfiltered
customthe solvent removed under vacuum
customThe crude product was purified by column chromatography on a Biotage instrument

Sources & evidence

ORD record: ord-9f6da2f7a2d44f14b3e47d1de4822787
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09273067B2

Reaction notes

Loading…