Chloride → HCID 10796854, compound

First, 65.1 g of 1,5-pentanediol, 18.6 g of proparygyl chloride, 12.0 g of sodium hydroxide (powdery), 5.69 g of benzyltriethylammonium chloride, and 200 ml of tetrahydrofuran were placed in a reaction vessel, and reaction mixture was stirred for 4 hours with heating under reflux. The reaction mixture was filtered through Celite, and the filtrate was poured into water, and extracted twice with diethyl ether. The diethyl ether layers were combined, washed with water, dried over anhydrous magnesium sulfate, and concentrated to give a crude product. This crude product was subjected to silica gel chromatography, which afforded 12.4 g (yield, 35%) of 5-(2-propynyloxy)pentanol, nD263 1.4533.

1. customreaction mixture
2. temperaturewith heating
3. temperatureunder reflux
4. filtrationThe reaction mixture was filtered through Celite
5. additionthe filtrate was poured into water
6. extractionextracted twice with diethyl ether
7. washwashed with water
8. dry with materialdried over anhydrous magnesium sulfate
9. concentrationconcentrated
10. customto give a crude product

ORD record

ord-f8a9bfa753944023b44c01dba83a03af

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06448444B1