D-Psicose → Methyl 6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-carboxylate

HRID 1643661Notes

Reaction equation

HRID 1643661 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([OH:17])[C:8](Br)=[C:9]2[O:13][C:12]([CH3:15])([CH3:14])[CH2:11][C:10]=12)=[O:4].OCC1(OC[C@@H](O)[C@@H](O)[C@H]1O)O>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([OH:17])[CH:8]=[C:9]2[O:13][C:12]([CH3:14])([CH3:15])[CH2:11][C:10]=12)=[O:4]

Participants

5

Reactant 2

HCID 441036D-PsicoseHCID 595601447-Bromo-6-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester

Product 1

HCID 59560026Methyl 6-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-4-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 7-bromo-6-hydroxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester (197d) (52 g, 0.17 mol) and 10% Pd on Carbon (5 g) in MeOH (1 L) was stirred under 50 Psi of H2 at 35-40° C. for 3 days. After HPLC indicated complete consumption of 197d, the reaction mixture was filtered through Celite and the filtrate was concentrated to give the title compound (30.6 g, 79.6%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 6.93 (s, 1H), 6.39 (s, 1H), 5.32 (s, 1H), 3.81 (s, 3H), 3.17 (s, 2 H), 1.40 (s, 6H).

Workup

  1. customconsumption of 197d
  2. filtrationthe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-12221676189748aba884fb57637f5ab6
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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