Water → 3-(Quinolin-2-ylmethoxy)-propan-1-ol

HRID 988261Notes

Reaction equation

[CH2:1]([OH:5])[CH2:2][CH2:3][OH:4].[H-].[Na+].Cl[CH2:9][C:10]1[CH:19]=[CH:18][C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=1.O>CN1C(=O)N(C)CCC1.C1COCC1>[N:11]1[C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:18]=[CH:19][C:10]=1[CH2:9][O:4][CH2:3][CH2:2][CH2:1][OH:5]

Participants

Conditions

Temperature: 0 °C

Procedure

1,3-Propanediol (6.0 mL, 85 mmol) is dissolved in 20% DMPU in THF (80 mL) and cooled to 0° C. Sodium hydride (60%, 3.6 mg, 90 mmol) is added portionwise, and the contents are allowed to stir for 15 min. at 0° C. 2-Chloromethylquinoline (7.64 g, 42.7 mmol) is added and the reaction is allowed to stir overnight. The reaction is poured into water (700 mL) and extracted with ethyl acetate (1×200 mL). Sodium chloride is added to the aqueous layer and extracted again with ethyl acetate (2×200 mL). The organic layers are pooled and washed with water (2×300 mL) and brine (2×300 mL), dried over MgSO4, filtered and reduced under vacuum to an oil. The crude material is purified by flash chromatography (silica, 2.5% methanol in dichloromethane) to give the title compound. MS (ESI) 218 (M+H)+.

Workup

stirringto stir overnight
extractionextracted with ethyl acetate (1×200 mL)
additionSodium chloride is added to the aqueous layer
extractionextracted again with ethyl acetate (2×200 mL)
washwashed with water (2×300 mL) and brine (2×300 mL)
dry with materialdried over MgSO4
filtrationfiltered
customThe crude material is purified by flash chromatography (silica, 2.5% methanol in dichloromethane)

Sources & evidence

ORD record: ord-0297c3260d0040abad637df1616461e8
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06635655B1

Reaction notes

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