Sodium Methoxide → Vanilloloside

HRID 707636Notes

Reaction equation

HRID 707636 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C@@H:13]2[O:30][C@H:29]([CH2:31][O:32]C(=O)C)[C@@H:24]([O:25]C(=O)C)[C@H:19]([O:20]C(=O)C)[C@H:14]2[O:15]C(=O)C)=[C:8]([O:36][CH3:37])[CH:7]=1)(=O)C.C[O-].[Na+]>CO>[C@@H:13]1([O:12][C:9]2[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[CH:7][C:8]=2[O:36][CH3:37])[O:30][C@H:29]([CH2:31][OH:32])[C@@H:24]([OH:25])[C@H:19]([OH:20])[C@H:14]1[OH:15]

Participants

4

Reactant 2

HCID 10942334Sodium Methoxide2×HCID 139653264-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-3-methoxybenzyl acetate

Product 1

HCID 44577222VanillolosideYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-methoxybenzyl acetate (7) (333 mg, 0.632 mmol) was suspended in methanol (2 ml), and sodium methoxide 5 M methanol solution (20 μl, 0.10 mmol) was added while cooling in an ice bath. The ice bath was removed and the mixture was warmed to room temperature and stirred for 2 hours. Sodium methoxide 0.5 M methanol solution (0.12 ml, 0.06 mmol) was further added and the mixture was stirred for 1 hour. The reaction solution was neutralized with a strong acidic cation exchange resin (Amberlite IR120B H AG). The resin was filtered off, and the filtrate was concentrated under reduced pressure to give 4-(β-D-glucopyranosyloxy)-3-methoxybenzyl alcohol (8) (147 mg, 0.465 mmol, yield 74%) as a colorless solid.

Workup

  1. temperaturewhile cooling in an ice bath
  2. customThe ice bath was removed
  3. stirringthe mixture was stirred for 1 hour
  4. filtrationThe resin was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-74247ff413df4d7da68f49ce5a27d0e2
Source dataset
uspto-grants-2015_11
Patent number
US09175028B2

Reaction notes

Loading…