Ethylene Oxide → HCID 19082053, compound

HRID 2273636Notes

Reaction equation

HRID 2273636 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][N:3]=1.[CH2:9]1[O:11][CH2:10]1.FC1C=C(CCO)C=CN=1>>[F:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 6354Ethylene OxideHCID 27374032-Fluoro-4-methylpyridineHCID 52951681HCID 52951681, compound

Product 1

HCID 19082053HCID 19082053, compoundYield 528.6%

Procedure

This compound was prepared, starting from compound 41 (7.00 g, 6.30 mmol) and ethylene oxide (4.20 mL, 84.1 mmol), according to the procedure developed for compound 42. The purification was performed using colomm chromatography (SiO2, AcOEt/pentane, 6/4, v/v) to give alcohol 48 (5.16 g, 33.3 mmol) as a yellow oil. Yield 53%; Rf (SiO2, AcOEt/pentane 6/4, v/v) 0.52; IR (CCl4) ν 1412, 1613, 2939, 3639 cm−1; 1H NMR (200 MHz, CDCl3) δ 1.84 (m, 2H), 2.72 (t, 2H, J=7.4 Hz), 3.14 (se, 1H), 3.62 (t, 2H, J=6.2 Hz), 6.72 (s, 1H), 6.98 (m, 1H), 8.01 (d, 1H, J=5.1 Hz); MS m/z 155 (M+, 6), 137 (25), 124 (12), 111 (100), 91 (21), 77 (14), 57 (14), 51 (16).

Workup

  1. customThis compound was prepared
  2. customThe purification

Sources & evidence

ORD record
ord-eb2b325c17e74ca5b6a9062685780dca
Source dataset
uspto-grants-2015_09
Patent number
US09125937B2

Reaction notes

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