Iodine → (E)-10-Iodo-2-(phenylmethylidene)deca-3,9-diyn-1-ol

HRID 1936914Notes

Reaction equation

[I:1]I.N1CCOCC1.[C:9]1(/[CH:15]=[C:16](\[C:19]#[C:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]#[CH:26])/[CH2:17][OH:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C1(C)C=CC=CC=1>[I:1][C:26]#[C:25][CH2:24][CH2:23][CH2:22][CH2:21][C:20]#[C:19]/[C:16](=[CH:15]\[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)/[CH2:17][OH:18]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of iodine (1.479 g, 5.83 mmol) in toluene (80 mL) was added morpholine (1.354 g, 15.54 mmol) followed by heating at 60° C. for 30 minutes. To the resultant mixture was added a solution of Compound 3 (462.3 mg, 1.94 mmol) in toluene (10 mL) and the mixture was heated at the same temperature for 6 hours. The reaction mixture was then allowed to cool down to room temperature and purified, without aqueous work up, by flash column chromatography (silica gel, 100 percent hexane and then 17 percent EtOAc in hexane) to give 630.3 mg (89 percent) of Compound 4: yellow oil; Rf=0.17 (17 percent EtOAc in hexane); IR (neat) 3362 (br), 2942, 2860, 2210, 1446, 1072 cm−1; 1H NMR (300 MHz, CDCl3) δ7.83-7.79 (m, 2H), 7.37-7.24 (m, 3H), 6.71 (s, 1H), 4.26 (d, J=1.20 Hz, 2H), 2.51-2.39 (m, 4H), 1.95 (br s, 1H), 1.76-1.62 (m, 4H); 13C NMR (75 MHz, CDCl3) δ136.7, 133.5, 129.1, 128.9, 128.8, 122.5, 98.7, 94.7, 79.4, 68.2, 28.3, 28.1, 21.0, 20.1, −5.9; MS (+CI) m/z (relative intensity) 365 (M+H+, 10), 220 (100); HRMS (+EI) calcd for C17H17IO 364.0324 (M+), found 364.0299.

Workup

temperaturethe mixture was heated at the same temperature for 6 hours
temperatureto cool down to room temperature
custompurified, without aqueous work up

Sources & evidence

ORD record: ord-9a4eb0a08da04cfd8dceb5b2244427df
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391916B1

Reaction notes

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