Sodium hydride → HCID 71009605, compound

HRID 1527244Notes

Reaction equation

HRID 1527244 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][OH:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH:14]([Si:17](Cl)([CH:21]([CH3:23])[CH3:22])[CH:18]([CH3:20])[CH3:19])([CH3:16])[CH3:15]>C1COCC1>[CH:14]([Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[N:1]1[C:9]2[C:4](=[CH:5][C:6]([CH2:10][O:11][Si:17]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[CH:14]([CH3:16])[CH3:15])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1)([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139400Triisopropylsilyl chlorideHCID 2773458(1H-indol-5-yl)methanol

Product 1

HCID 71009605HCID 71009605, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1H-indol-5-yl)-methanol (1.00 g, 6.79 mmol) in THF (60 mL), cooled to 0° C., was added sodium hydride (60% in mineral oil; 1.36 g, 34.0 mmol) portionwise. After stirring for 5 min, triisopropylsilyl chloride (2.88 mL, 13.6 mmol) was added, and the resulting solution was stirred at RT for 2 h. The reaction was quenched by addition of a saturated aqueous NaHCO3 solution at 0° C. The aqueous layer was repeatedly extracted with EtOAc, and the combined organics were washed with H2O (1×) and brine (1×), dried (phase separator) and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluent gradient: c-hexane to c-hexane/EtOAc 9:1) afforded the title compound as a white solid. TLC, Rf (c-hexane/EtOAc 9:1)=0.72. 1H-NMR (400 MHz, DMSO-d6): 5 ppm 7.61 (s, 1H), 7.49 (d, 1H), 7.32 (d, 1H), 6.93 (d, 1H), 6.57 (d, 1H), 4.92 (s, 2H), 1.60-1.85 (m, 3H), 1.01-1.12 (m, 39H).

Workup

  1. stirringthe resulting solution was stirred at RT for 2 h
  2. customThe reaction was quenched by addition of a saturated aqueous NaHCO3 solution at 0° C
  3. extractionThe aqueous layer was repeatedly extracted with EtOAc
  4. washthe combined organics were washed with H2O (1×) and brine (1×)
  5. customdried (phase separator)
  6. concentrationconcentrated in vacuo
  7. customPurification by flash column chromatography on silica gel (eluent gradient: c-hexane to c-hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-c1a27ed24bd441c8a96272ab9f1678ed
Source dataset
uspto-grants-2015_07
Patent number
US09085555B2

Reaction notes

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