(NZ)-N-(5-ethyl-6,7-dihydro-5H-1-benzofuran-4-ylidene)hydroxylamine → cis 5-Ethyl-4,5,6,7-tetrahydro-1-benzofuran-4-amine

HRID 1824077Notes

Reaction equation

HRID 1824077 reaction equation
C([C@@H]1[C@H](N)C2C=CSC=2CC1)CC.[CH2:14]([CH:16]1[CH2:17][CH2:18][C:19]2[O:23][CH:22]=[CH:21][C:20]=2/[C:24]/1=[N:25]\O)[CH3:15]>>[CH2:14]([C@@H:16]1[C@H:24]([NH2:25])[C:20]2[CH:21]=[CH:22][O:23][C:19]=2[CH2:18][CH2:17]1)[CH3:15]

Participants

3

Reactant 2

HCID 58583259(NZ)-N-(5-ethyl-6,7-dihydro-5H-1-benzofuran-4-ylidene)hydroxylamineHCID 58583416cis-5-Propyl-4,5,6,7-tetrahydro-1-benzothiophen-4-amine

Product 1

HCID 86588867cis 5-Ethyl-4,5,6,7-tetrahydro-1-benzofuran-4-amine

Procedure

Following the procedure for the preparation of cis-5-propyl-4,5,6,7-tetrahydro-1-benzothiophen-4-amine but substituting (4E) and (4Z)-5-ethyl-6,7-dihydro-1-benzofuran-4(5H)-one oxime and making non-critical variations provided the title compound as a oil: 1H NMR (CDCl3) δ 1.02, 1.30–1.73, 2.50–2.67, 3.84, 6.38, 7.27; HRMS (FAB) calcd for C10H15NO+H 166.1232, found 166.1231. Anal. Calcd for C10H15NO: C, 72.69; H, 9.15; N, 8.48. Found: C, 72.33; H, 9.14; N, 8.08.

Sources & evidence

ORD record
ord-eeb3fc05b8e341969542410decaa4448
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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