m-Ethylbenzaldehyde → (5-ethyl-2-fluorophenyl)(5-phenyl-2-trityl-2H-1,2,4-triazol-3-yl)methanol

HRID 2105060Notes

Reaction equation

C(C1C=C(C=CC=1)C=O)C.[C:11]1([C:17]2[N:21]=[CH:20][N:19]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:41]([C:43]1[CH:44]=[CH:45][C:46]([F:51])=[C:47]([CH:50]=1)[CH:48]=[O:49])[CH3:42]>>[CH2:41]([C:43]1[CH:44]=[CH:45][C:46]([F:51])=[C:47]([CH:48]([C:20]2[N:19]([C:22]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:18]=[C:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[N:21]=2)[OH:49])[CH:50]=1)[CH3:42]

Participants

Reactant 3

HCID 118623m-Ethylbenzaldehyde

HCID 578038035-Ethyl-2-fluorobenzaldehyde

HCID 688125613-phenyl-1-trityl-1H-1,2,4-triazole

Product 1

HCID 57803662(5-ethyl-2-fluorophenyl)(5-phenyl-2-trityl-2H-1,2,4-triazol-3-yl)methanolYield 82.5%

Procedure

According to the procedure for Intermediate 370.1, 3-phenyl-1-trityl-1H-1,2,4-triazole (250 mg, 0.66 mmol) and 5-ethyl-2-fluorobenzaldehyde (100 mg, 0.66 mmol) afforded 294 mg of Intermediate 384.1 as a white solid. 1H NMR (400 MHz, CD3OD) δ ppm 1.06 (t, J=7.70 Hz, 3H) 2.41 (q, J=7.58 Hz, 2H) 2.89 (d, J=9.05 Hz, 1H) 5.41 (d, J=9.29 Hz, 1H) 6.60 (dd, J=9.90, 8.44 Hz, 1H) 6.82-6.93 (m, 1H) 6.96 (dd, J=7.34, 2.20 Hz, 1H) 7.02-7.09 (m, 6H) 7.09-7.16 (m, 9H) 7.24-7.39 (m, 4H) 7.98-8.10 (m, 2H).

Sources & evidence

ORD record: ord-d006103be3444a5c9685add75f0b3b62
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576098B2

Reaction notes

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