Diethyl Ether → 3-((Tert-butyldiphenylsilyl)oxy)-2-fluoropropan-1-OL

HRID 1867460Notes

Reaction equation

HRID 1867460 reaction equation
[H-].[Na+].[F:3][CH:4]([CH3:8])[CH:5]([OH:7])O.[Si:9](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CC[O:29]CC>C1COCC1>[Si:9]([O:29][CH2:8][CH:4]([F:3])[CH2:5][OH:7])([C:22]([CH3:25])([CH3:24])[CH3:23])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 94078tert-ButyldiphenylchlorosilaneHCID 866199192-Fluoropropane-1,1-diol

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a flask filled with THF (20 mL) was added sodium hydride (0.255 mg, 10.62 mmol) followed by the addition of 2-fluoropropanediol (1.0 g, 10.62 mmol) in THF. The reaction was stirred for 45 minutes followed by the addition of tert-butyldiphenylsilylchloride (2.92 g, 10.628 mmol) and stirred vigorously for another 45 min as the reaction gradually approaches room temperature. The reaction mixture was poured into a separatory funnel filled ⅓ of the way with ether and extracted with 15% K2CO3, washed with brine and dried over sodium sulfate. The resulting clear oil was purified by column chromatography (SiO2; 0%->30% EtOAc:Hx to provide the title compound as a clear oil. 1H NMR (500 MHz, CDCl3) δ 1.56 (s, 9H), 3.83-3.93 (m, 4H), 4.58-4.69 (d, J=52 Hz, 1H), 7.39-7.47 (m, 6H), 7.72-7.73 (m, 4H) ppm. HRMS [M+H] C19H25FO2Si calc'd 333.1681, found 333.1667.

Workup

  1. stirringstirred vigorously for another 45 min as the reaction gradually approaches room temperature
  2. additionThe reaction mixture was poured into a separatory funnel
  3. extractionextracted with 15% K2CO3
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe resulting clear oil was purified by column chromatography (SiO2

Sources & evidence

ORD record
ord-e858b7d9a9024b84a1000e188e518a88
Source dataset
uspto-grants-2009_12
Patent number
US07632839B2

Reaction notes

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