Triacetoxyperiodinane → 3-{[Tert-butyl(diphenyl)silyl]oxy}-2-fluoropropanal

HRID 1867461Notes

Reaction equation

HRID 1867461 reaction equation
[Si:1]([O:18][CH2:19][CH:20]([F:23])[CH2:21][OH:22])([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.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl>[Si:1]([O:18][CH2:19][CH:20]([F:23])[CH:21]=[O:22])([C:14]([CH3:17])([CH3:15])[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

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 579797963-((Tert-butyldiphenylsilyl)oxy)-2-fluoropropan-1-OL

Product 1

HCID 111421123-{[Tert-butyl(diphenyl)silyl]oxy}-2-fluoropropanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 3-{[tert-butyl(diphenyl)silyl]oxy}-2-fluoropropan-1-ol (0.900 g, 2.707 mmol) in dichloromethane (13.5 mL) was added Dess-Martin Periodinane (1.72 g, 4.06 mmol). The reaction was stirred for 40 minutes and then quenched with Na2S2O3 (2.0 M aqueous solution) and saturated sodium bicarbonate. The reaction was partitioned into dichloromethane and water and the organic solution dried over sodium sulfate. The organic solution was filtered and concentration to afford the title compound as a clear oil. 1H NMR (500 MHz, CDCl3) δ 1.05 (s, 9H), 4.02-4.12 (m, 2H), 4.75-5.07 (m, 1H), 7.35-7.44 (m, 6H), 7.64-7.69 (m, 4H), 9.85-9.86 (m, 1H) ppm.

Workup

  1. customquenched with Na2S2O3 (2.0 M aqueous solution) and saturated sodium bicarbonate
  2. customThe reaction was partitioned into dichloromethane and water
  3. dry with materialthe organic solution dried over sodium sulfate
  4. filtrationThe organic solution was filtered
  5. concentrationconcentration

Sources & evidence

ORD record
ord-5eb8eebf89234be48d924174dfa8ff30
Source dataset
uspto-grants-2009_12
Patent number
US07632839B2

Reaction notes

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