8-[(E)-2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one → 8-(3,4-Dihydroxy-butyl)-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one

HRID 2275298Notes

Reaction equation

HRID 2275298 reaction equation
CC1(C)[O:6][CH:5](/[CH:7]=[CH:8]/[C:9]2[CH:10]=[C:11]3[C:23](=[CH:24][CH:25]=2)[C:22](=[O:26])[C:14]2[C:15]4[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=4[O:17][C:13]=2[C:12]3([CH3:28])[CH3:27])[CH2:4][O:3]1>[Pd].CO>[OH:6][CH:5]([CH2:4][OH:3])[CH2:7][CH2:8][C:9]1[CH:10]=[C:11]2[C:23](=[CH:24][CH:25]=1)[C:22](=[O:26])[C:14]1[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]=3[O:17][C:13]=1[C:12]2([CH3:28])[CH3:27]

Participants

4

Reactant 1

HCID 668341018-[(E)-2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-vinyl]-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one

Product 1

HCID 668351218-(3,4-Dihydroxy-butyl)-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-oneYield 31%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To the MeOH solution (5 ml) of 8-[(E)-2-(2,2-dimethyl-[1,3]dioxolan-4-yl)-vinyl]-6,6-dimethyl-6H-benzo[b]naphtho[2,3-d]furan-11-one (125 mg), 10% Pd—C (25 mg) was added and the mixture was stirred overnight at room temperature under hydrogen atmosphere. The catalyst was removed by filtration. The residues obtained after concentration under reduced pressure were purified by HPLC to obtain the title compound (35 mg, 31%).

Workup

  1. customThe catalyst was removed by filtration
  2. customThe residues obtained
  3. concentrationafter concentration under reduced pressure
  4. customwere purified by HPLC

Sources & evidence

ORD record
ord-673b496aa03b4259812ba940baa34f75
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

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