HCID 13961928, compound → HCID 44280460, compound

HRID 246911Notes

Reaction equation

HRID 246911 reaction equation
[CH2:1]([C:4]1[C:5]([OH:24])=[CH:6][C:7]2[O:11][CH:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[CH:9]([CH3:22])[C:8]=2[CH:23]=1)[CH:2]=[CH2:3]>C(OCC)(=O)C.[Pd]>[OH:24][C:5]1[C:4]([CH2:1][CH2:2][CH3:3])=[CH:23][C:8]2[C@H:9]([CH3:22])[C@@H:10]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)[O:11][C:7]=2[CH:6]=1

Participants

4

Reactant 1

HCID 13961928HCID 13961928, compound

Product 1

HCID 44280460HCID 44280460, compoundYield 93.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Rac-(2S,3S)-5-allyl-6-hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-2,3-dihydrobenzofuran (1.28 g) in ethyl acetate (30 ml) containing 10% palladium-on-charcoal (40 mg) was hydrogenated at 20 p.s.i. for 2 hours. The mixture was filtered and the filtrate was evaporated to give (2S,3S)-6-Hydroxy-2-(3,4-dimethoxyphenyl)-3-methyl-5-propyl-2,3-dihydrobenzofuran (1.2 g); n.m.r. (CDCl3): δ0.99 (t, CH2CH2CH3), 1.37 (d, CH3 --3), 1.65 (m, CH2CH2CH3), 2.55 (t, CH2CH2CH3), 3.38 (m, H-3), 3.90, 3.91 (s, s, 2OCH3), 4.69 (b, OH), 5.07 (d, J 9.0 Hz, H-2), 6.06-7.01 (Ar--H), 6.38 (s, H-7).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-749fbce5a1454346ac7e391457e22646
Source dataset
uspto-grants-1987_11
Patent number
US04704462

Reaction notes

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