Pyridine → HCID 53788510, compound

HRID 1197356Notes

Reaction equation

HRID 1197356 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH2:7]([OH:11])[CH2:8][C:9]#[CH:10].[OH:12][CH2:13][C:14]1([CH2:18][CH2:19][CH3:20])[CH2:17][O:16][CH2:15]1.N1C=CC=CC=1>ClCCl.O>[C:1]([O:11][CH2:7][CH2:8][C:9]#[CH:10])(=[O:5])[C:2]([O:12][CH2:13][C:14]1([CH2:18][CH2:19][CH3:20])[CH2:17][O:16][CH2:15]1)=[O:3]

Participants

7

Reactant 4

HCID 1049PyridineHCID 135663-Butyn-1-OLHCID 65578Oxalyl chlorideHCID 1838902-Propyl-2-oxetanemethanol

Product 1

HCID 53788510HCID 53788510, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Oxalyl chloride (4.3 ml) was added to a stirred solution of but-3-yn-1-ol (3.5 g) in dry dichloromethane (75 ml), at 0°. The solution was stirred at 0° for 30 minutes and was then added, dropwise to a stirred solution of 3-hydroxymethyl-3-n-propyloxetane (6.4 g) and dry pyridine (30 ml) in dry dichloromethane (75 ml). The mixture was stirred at 20° for 24 hours. Water was added and the aqueous mixture was extracted with diethyl ether. The ethereal extracts were washed with 5% hydrochloric acid solution, saturated sodium hydrogen carbonate solution and finally water. The ethereal extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. The resulting oil was chromatographed on silica (pre-eluted with 1% triethylamine in hexane), and eluting with 1:1 diethyl ether:hexane. But-3-ynyl (3-n-propyloxetan-3-yl)methyl oxalate was obtained as a colourless oil (7.0 g).

Workup

  1. stirringThe mixture was stirred at 20° for 24 hours
  2. extractionthe aqueous mixture was extracted with diethyl ether
  3. washThe ethereal extracts were washed with 5% hydrochloric acid solution, saturated sodium hydrogen carbonate solution and finally water
  4. dry with materialThe ethereal extracts were dried over anhydrous magnesium sulphate
  5. customevaporated in vacuo
  6. customThe resulting oil was chromatographed on silica (pre-eluted with 1% triethylamine in hexane)
  7. washeluting with 1:1 diethyl ether

Sources & evidence

ORD record
ord-e6b2767757ab4598a8a1e97de0ceffcd
Source dataset
uspto-grants-1992_05
Patent number
US05116862

Reaction notes

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