Ethyl isocyanate → 8-(4,5,6,7-Tetramethoxyindan-2-yl)octyl N-ethylcarbamate

HRID 2268471Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]([O:16][CH3:17])=[C:8]2[C:4]=1[CH2:5][CH:6]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])[CH2:7]2.[CH2:27]([N:29]=[C:30]=[O:31])[CH3:28]>C1COCC1.N1C=CC=CC=1>[CH2:27]([NH:29][C:30](=[O:31])[O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH:6]1[CH2:7][C:8]2[C:4](=[C:3]([O:2][CH3:1])[C:11]([O:12][CH3:13])=[C:10]([O:14][CH3:15])[C:9]=2[O:16][CH3:17])[CH2:5]1)[CH3:28]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of 8-(4,5,6,7-tetramethoxyindan-2-yl)octanol (1.20 g) and ethyl isocyanate (0.517 ml) in THF (12 ml) was added one drop of pyridine. After being stirred for 12 hr at 40° C., the reaction mixture was concentrated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to yield the entitled compound (1.42 g) as crystals.

Workup

concentrationthe reaction mixture was concentrated in vacuo
customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-5a13142331894737a49a84e624dba603
Source dataset: uspto-grants-2001_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06326369B1

Reaction notes

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