1-Heptyne → HCID 25221951, compound

HRID 1967198Notes

Reaction equation

HRID 1967198 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1OS(C1C=CC(C)=CC=1)(=O)=O)=[O:4].[CH:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]>CCCCCCC.C(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[C:21]#[C:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:4]

Participants

4

Reactant 2

HCID 123501-HeptyneHCID 2808173HCID 2808173, compound

Product 1

HCID 25221951HCID 25221951, compound

Reagents, catalysts & solvents 1

HCID 21907733Dichloromethane heptaneSolvent

Procedure

This product was prepared from 3-(toluene-4-sulfonyloxy)-thiophene-2-carboxylic acid methyl ester and 1-heptyne following the general procedure for the Sonogashira cross-coupling reaction described above. Chromatography eluent: heptane/DCM 1:1; yield (71 mg, 60%); 1H NMR δ (CDCl3): 7.32 (d, J=5.03 Hz, 1H), 7.01 (d, J=5.10 Hz, 1H), 3.81 (s, 3H), 2.42 (t, J=7.25 Hz, 2H), 1.57 (p, J=7.19 Hz, 2H), 1.45-1.26 (m, 4H), 0.87 (t, J=7.2 Hz, 3H); LCMS m/z: 236.

Workup

  1. customfor the Sonogashira cross-coupling reaction
  2. customyield (71 mg, 60%)

Sources & evidence

ORD record
ord-17b8c670a9304d2eaa231dbf0e37c3e1
Source dataset
uspto-grants-2013_04
Patent number
US08420812B2

Reaction notes

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