HCID 10988699, compound → 1,6-dioxacyclododec-9-yne-2,5-dione

HRID 879937Notes

Reaction equation

HRID 879937 reaction equation
[CH2:1]([O:6][C:7](=[O:18])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH2:14][C:15]#[C:16][CH3:17])=[O:11])CC#CC>C1(C)C=CC=CC=1>[O:6]1[CH2:1][CH2:17][C:16]#[C:15][CH2:14][CH2:13][O:12][C:10](=[O:11])[CH2:9][CH2:8][C:7]1=[O:18]

Participants

3

Reactant 1

HCID 10988699HCID 10988699, compound

Product 1

HCID 118303421,6-dioxacyclododec-9-yne-2,5-dione

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

In a dry 500 mL Schlenk-tube, which has been flooded with argon, succinic acid dipent-3-inyl ester (5.00 mmol, 1.251 g), [Mo(≡N)(OSiPh3)3(phen)].0.5 toluene (0.500 mmol, 581.2 mg), MnCl2 (0.500 mmol, 62.9 mg) and molecular sieve (10.0 g, 5 Å, powder) were suspended in 250 mL of toluene. The reaction solution was stirred for 24 h at 80° C. and was filtered after cooling over a short silica gel column. The filtrate was concentrated and the residue was purified by means of column chromatography (hexane/EtOAc 4:1). 1,6-dioxacyclododec-9-in-2,5-dione was isolated as colorless oil (yield 60%). 1H NMR (400 MHz, CD2Cl2): δ=4.21-4.14 (m, 4H), 2.61 (s, 4H), 2.44-2.37 (m, 4H); 13C NMR (100 MHz, CD2Cl2): δ=171.9 (2×C), 79.0 (2×C), 61.6 (2×CH2), 30.2 (2×CH2), 19.7 (2×CH2); IR (film): v=2965, 2915, 2840, 1729, 1458, 1421, 1383, 1353, 1336, 1267, 1251, 1158, 1053, 1030, 1000, 952, 837 cm−1; MS (EI) m/z (%): 166 (1), 101 (14), 78 (100), 66 (59), 65 (16), 55 (7), 40 (12), 28 (7); HRMS (ESI): m/z: calculated for C10H12O4+Na: 219.0628; found: 219.0627.

Workup

  1. filtrationwas filtered
  2. temperatureafter cooling over a short silica gel column
  3. concentrationThe filtrate was concentrated
  4. customthe residue was purified by means of column chromatography (hexane/EtOAc 4:1)

Sources & evidence

ORD record
ord-3ae49762d819459f878c1e244bd4361c
Source dataset
uspto-grants-2015_03
Patent number
US08993470B2

Reaction notes

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