Methanol → HCID 12770868, compound
Reaction equation
[CH3:1][O:2][C:3]1([CH2:10][CH2:11][C:12](OCC)=[O:13])[CH:7]=[CH:6][CH:5]([O:8][CH3:9])[O:4]1.[H-].C([Al+]CC(C)C)C(C)C.CO.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1(C)C=CC=CC=1.O>[CH3:1][O:2][C:3]1([CH2:10][CH2:11][CH:12]=[O:13])[CH:7]=[CH:6][CH:5]([O:8][CH3:9])[O:4]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -75 °C
Procedure
To a stirred solution of 48.9 g. of 2,5-dihydro-2,5-dimethoxy-2-(2'-carbethoxyethyl)furan (Example 1) in 800 ml. of toluene was added 263 ml. of 0.89M diisobutylaluminum hydride in toluene during 90 minutes at -75°C. The solution was stirred at -75°C. for 30 minutes and then treated with 5.0 ml. of methanol. The stirred solution is treated with 100 ml. of water, and the resulting mixture is stirred at 0°-5°C. for 15 minutes, saturated with sodium sulfate, and filtered through Celite with the aid of ethyl acetate. The filtrate is washed with brine, dried over magnesium sulfate, and concentrated. The residue is distilled to provide a light yellow liquid, b.p. 76°-78°C. (0.25 mm.), ν max 1725 (aldehyde carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group).
Workup
- additiontreated with 5.0 ml
- additionThe stirred solution is treated with 100 ml
- filtrationfiltered through Celite with the aid of ethyl acetate
- washThe filtrate is washed with brine
- dry with materialdried over magnesium sulfate
- concentrationconcentrated
- distillationThe residue is distilled
- customto provide a light yellow liquid, b.p. 76°-78°C. (0.25 mm.), ν max 1725 (aldehyde carbonyl group) and 1015 cm-1 (dimethoxydihydrofuran group)
Sources & evidence
- ORD record
- ord-3c49f31b562c46d29e5e55bae743f982
- Source dataset
- uspto-grants-1976_04
- Patent number
- US03952033
Reaction notes
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