6-(hydroxymethyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one → 3-oxo-3,6,7,8-tetrahydro-1H-indeno[4,5-c]furan-6-carbaldehyde
Reaction equation
[OH:1][CH2:2][CH:3]1[C:7]2[CH:8]=[CH:9][C:10]3[C:14](=[O:15])[O:13][CH2:12][C:11]=3[C:6]=2[CH2:5][CH2:4]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.I([O-])(=O)(=O)=O>C(Cl)Cl>[O:15]=[C:14]1[O:13][CH2:12][C:11]2[C:6]3[CH2:5][CH2:4][CH:3]([CH:2]=[O:1])[C:7]=3[CH:8]=[CH:9][C:10]1=2Participants
4
Procedure
To a solution of 6-(hydroxymethyl)-1,6,7,8-tetrahydro-3H-indeno[4,5-c]furan-3-one (55 mg, 0.27 mmol) in DCM (5 mL) was added Dess-Martin Periodate (171 mg, 0.400 mmol). The reaction was allowed to stir at RT for 3 hours. LC analysis showed formation of the desired product, and there was little SM left. The solution was diluted with DCM (30 mL), and to that was added Na2S2O3 (10% aq solution, 15 mL) to consume the excess Dess-Martin reagent. The mixture was stirred until the two layers separated. The bottom DCM layer was collected, washed with aq Na2CO3, dried over sodium sulfate, and concentrated to give 3-oxo-3,6,7,8-tetrahydro-1H-indeno[4,5-c]furan-6-carbaldehyde. LC-MS (IE, m/z): 203 [M+1]+; tR=0.58 min.
Sources & evidence
- ORD record
- ord-56bcc33dab104d4fbf3dcc99c5de2462
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018211B2
Reaction notes
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