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

HRID 268429Notes

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

Reactant 3

HCID 8028Tetrahydrofuran

HCID 144156756-Acetoxy-2,5,7,8-tetramethyl-2-cyanochromane

HCID 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-efaa266f25fb4649907605182e398c8f
Source dataset: uspto-grants-1976_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03947473

Reaction notes

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