Tetrahydrofuran → (+/-)-6-Acetoxy-2,5,7,8-tetramethylchroman-2-carboxaldehyde

HRID 2399070Notes

Reaction equation

HRID 2399070 reaction equation
[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([C:18]#N)([CH3:17])[CH2:9][CH2:8]2)(=[O:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.[O:31]1CCCC1>>[C:1]([O:4][C:5]1[C:6]([CH3:20])=[C:7]2[C:12](=[C:13]([CH3:16])[C:14]=1[CH3:15])[O:11][C:10]([CH3:17])([CH:18]=[O:31])[CH2:9][CH2:8]2)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 144156756-Acetoxy-2,5,7,8-tetramethyl-2-cyanochromaneHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 15818868(+/-)-6-Acetoxy-2,5,7,8-tetramethylchroman-2-carboxaldehyde

Procedure

(±)-6-acetoxy-2-cyano-2,5,7,8-tetramethylchroman was reduced with diisobutylaluminum hydride as described in Example 101, with tetrahydrofuran as reaction solvent. TLC of the crude product indicated that it was partially deacetylated. The material was thus reacetylated by the process described in Example 2 to give (±)-6-acetoxy-2,5,7,8-tetramethylchroman-2-carboxaldehyde as a white solid, m.p. 88°-90°, from 30°-60° petroleum ether.

Sources & evidence

ORD record
ord-2b3bafd33ff745148a64951b06254a14
Source dataset
uspto-grants-1977_05
Patent number
US04026907

Reaction notes

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