Diethyl Ether → HCID 10130730, compound

HRID 879938Notes

Reaction equation

HRID 879938 reaction equation
[CH2:1]([O:6][C:7](=[O:20])[CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH2:16][C:17]#[C:18][CH3:19])=[O:13])CC#CC.O(CC)CC>C1(C)C=CC=CC=1>[O:6]1[CH2:1][CH2:19][C:18]#[C:17][CH2:16][CH2:15][O:14][C:12](=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:20]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 11087095Hexanedioic acid, di-3-pentynyl ester

Product 1

HCID 10130730HCID 10130730, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a dry 100 mL Schlenk-tube, which has been flooded with argon, adipic acid dipent-3-inyl ester (135 mg, 485 μmol), complex 23a.OEt2 (10.5 mg, 9.67 μmol, 2 mol %) and molecular sieve (970 mg, 5 Å, powder) were suspended in 24.2 mL of toluene. The reaction solution was stirred for 24 h at room temperature, was filtered for the processing over a short silica gel column, the filtrate was concentrated and the residue was purified by means of column chromatography (SiO2, hexane/EtOAc, 20:1). One obtains 1,8-dioxacyclotetradec-11-in-2,7-dione (100 mg, 92%) as colorless solid. M.p.=109-110° C.; 1H NMR (400 MHz, CD2Cl2): δ=4.13-4.06 (m, 4H), 2.53-2.47 (m, 4H), 2.39-2.30 (m, 4H), 1.76-1.67 (m, 4H); 13C NMR (100 MHz, CD2Cl2): δ=173.2 (2×C), 78.2 (2×C), 62.8 (2×CH2), 35.2 (2×CH2), 25.4 (2×CH2), 19.4 (2×CH2); IR (film): v=2995, 2954, 2937, 2918, 2901, 2872, 1721, 1458, 1425, 1384, 1341, 1272, 1236, 1167, 1140, 1080, 1065, 1021, 981, 931, 843, 124, 699 cm−1; MS (EI) m/z (%): 129 (3), 111 (8), 78 (100), 66 (20), 55 (15), 41 (8); HRMS (ESI): m/z: calculated for C12H16O4+Na: 247.0941; found: 247.0938.

Workup

  1. filtrationwas filtered for the processing over a short silica gel column
  2. concentrationthe filtrate was concentrated
  3. customthe residue was purified by means of column chromatography (SiO2, hexane/EtOAc, 20:1)

Sources & evidence

ORD record
ord-38cfa5aad652472eaadcbd259dbb97e6
Source dataset
uspto-grants-2015_03
Patent number
US08993470B2

Reaction notes

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