Triphenylphosphine → HCID 54271202, compound
Reaction equation
CCOC(/N=N/C(OCC)=O)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:32][O:33][C:34]1[CH:35]=[C:36]2[C:41](=[CH:42][CH:43]=1)[CH:40]=[C:39]([CH:44]([CH3:47])[CH2:45][OH:46])[CH:38]=[CH:37]2.[C:48](O)(=[S:50])[CH3:49]>C1COCC1.C(OCC)(=O)C>[C:48]([O:46][CH2:45][CH:44]([C:39]1[CH:38]=[CH:37][C:36]2[C:41](=[CH:42][CH:43]=[C:34]([O:33][CH3:32])[CH:35]=2)[CH:40]=1)[CH3:47])(=[S:50])[CH3:49]Participants
Procedure
To a solution of diethylazodicarboxylate (4.03 g, 23.14 mmol) and triphenyl phosphine (6.06 g, 23.14 mmol) at 0° C. in THF (50 mL) was added 2-(6-methoxy-2-naphthyl)propan-1-ol (2.5 g, 11.57 mmol) and thioacetic acid (1.76 g, 23.14 mmol). The reaction mixture was stirred for 30 minutes before it was allowed to warm to room temperature and then stirred overnight. The reaction mixture was diluted with ethyl acetate ("EtOAc") (100 mL) and washed with water (100 mL). The organic layer was dried (MgSO4) and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, ethyl acetate-hexane (1:9)) to give 1.5 g of the title compound as an oil. 1H NMR (CDCl3)δ1.38 (d, 3 H, CH3), 2.29 (s, 3 H, SCH3), 3.10 (m, 1 H), 3.18 (m, 2 H), 3.91 (s, 3 H, OCH3), 7.11-7.72 (m, 6 H).
Workup
- stirringstirred overnight
- washwashed with water (100 mL)
- dry with materialThe organic layer was dried (MgSO4)
- concentrationconcentrated under reduced pressure
- customThe residue was purified by flash chromatography (silica gel, ethyl acetate-hexane (1:9))
Sources & evidence
- ORD record
- ord-771d292ea16f4bb4871204ab014135ee
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05925673
Reaction notes
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