Hexane → HCID 89543862, compound

HRID 1750754Notes

Reaction equation

HRID 1750754 reaction equation
[Si:1]([C:8]1[C:17]([CH:18]=[O:19])=[C:16]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=[CH:15]2)[C:9]=1[CH:20]=[O:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:22]([C:28]([O:30][CH3:31])=[O:29])#[C:23][C:24]([O:26][CH3:27])=[O:25].[CH:32]1([N+:38]#[C-:39])[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1.CCCCCC>C1C=CC=CC=1.C(OC(=O)C)C>[CH3:27][O:26][C:24]([C:23]1[C:22]([C:28]([O:30][CH3:31])=[O:29])=[C:39]([NH:38][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[O:19][C:18]=1[C:17]1[C:16]2[C:10]([CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[C:9]([CH:20]=[O:21])[C:8]=1[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])=[O:25]

Participants

7

Reactant 4

HCID 8058HexaneHCID 12980Dimethyl acetylenedicarboxylateHCID 79129Cyclohexyl isocyanideHCID 89545285HCID 89545285, compound

Product 1

HCID 89543862HCID 89543862, compoundYield 25.3%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

According to the literature procedure, a mixture of 250 mg of bis-dialdehyde 32 (0.84 mmol) and 92 mg of DMAD (dimethyl acetylenedicarboxylate) (0.84 mmol) was dissolved in 8.5 ml of anhydrous benzene and heated at 80° C. under argon. To this solution was added 119 mg of cyclohexylisocyanide (0.84 mmol) by syringe, and the heating was continued at 80° C. for further 5 days. The color of the reaction changed from red into brown. The solvent was then evaporated in vacuo, and the crude residue was purified on column chromatography using 8:2 hexane:ethylacetate to obtain first starting material, and then polarity was increased to 7:3 hexane:ethylacetate to furnish 117 mg of 50 as wine red solid in 25% yield. 1H NMR δ 10.59 (s, 1H), 9.99 (dd, 1H, J=9.9, 0.8), 8.40 (dd, 1H, J=9.9, 0.8), 7.90 (t, 1H, J=9.8), 7.71 (t, 1H, J=9.8), 7.40 (t, 1H, J=9.7), 6.72 (d, 1H, J=8.9), 3.82 (s, 3H), 3.52-3.365 (m, 1H), 3.49 (s, 3H), 1.20-2.05 (m, 10H), 0.95 (s, 9H), 0.34 (s, 3H), 0.23 (s, 3H); 13C NMR δ 189.84, 165.34, 164.39, 162.04, 157.31, 146.20, 141.70, 141.15, 139.83, 139.73, 138.19, 131.24, 130.20, 129.45, 125.96, 118.56, 86.09, 51.74, 51.35, 51.03, 34.01, 33.89, 27.34, 25.27, 24.69, 24.60, 17.95, −1.86, −3.42; LRMS (LC/MS-ESI, MeOH) m/e 550 (MH+)

Workup

  1. customThe solvent was then evaporated in vacuo
  2. customthe crude residue was purified on column chromatography
  3. customethylacetate to obtain first

Sources & evidence

ORD record
ord-7fb588eaebf1470c9d573b6f2a0f7b45
Source dataset
uspto-grants-2015_10
Patent number
US09156862B2

Reaction notes

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