4-Hydroxybenzaldehyde → HCID 23397581, compound

HRID 968438Notes

Reaction equation

HRID 968438 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[OH-].[Na+].O.[C:13]([O:16][C@H:17]1[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:21]([O:27][C:28](=[O:30])[CH3:29])[CH2:20][O:19][C@H:18]1Br)(=[O:15])[CH3:14]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[C:13]([O:16][C@H:17]1[C@H:22]([O:23][C:24](=[O:26])[CH3:25])[C@H:21]([O:27][C:28](=[O:30])[CH3:29])[CH2:20][O:19][C@H:18]1[O:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)(=[O:15])[CH3:14]

Participants

7

Reactant 4

HCID 1264-HydroxybenzaldehydeHCID 962WaterHCID 14798Sodium HydroxideHCID 110782882,3,4-Tri-O-acetylpentopyranosyl bromide

Product 1

HCID 23397581HCID 23397581, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

p-Hydroxybenzaldehyde (2.2 g, 18 mmol), dichloromethane 18 mL, a 5% aqueous solution of sodium hydroxide (20 mL) were put in a 100 mL round bottom flask and stirred vigorously. At that time, a water phase turned yellow. To the resulting mixture, tetrabutylammonium bromide (1.0 g, 3.0 mmol) was added, and then a solution of 2,3,4-tri-O-acetyl-β-D-arabinopyranosyl bromide (4.0 g, 12 mmol) in dichloromethane (about 6 mL) was added dropwise. A reaction vessel was prptected from light, and the resulting mixture was stirred vigorously at room temperature for 2 days. The separated organic phase was washed with 50 mL of a 5% aqueous solution of sodium hydroxide three times and then with 50 mL of water three times, dried over anhydrous sodium sulfate and evaporated to dryness to give the title compound. Light brown solid. Yield 1.9 g, 43%. The product was unstable at room temperature, and stored in the freezer. 1H NMR (300.07 MHz, CDCl3) δ: 9.92 (1H, s, aldehyde), 7.86 (2H, d, J=8.4 Hz, o-aldehyde), 7.13 (2H, d, J=8.7, m-aldehyde), 5.45 (1H, d, J=6.0, 8.1 Hz, H-2′), 5.36 (1H, m, H-4′), 5.24 (1H, d, J=6.0 Hz, H-1′), 5.20 (1H, dd, J=3.6, 8.4 Hz, H-3′), 4.13 (1H, dd, J=4.2, 12.3 Hz, H-5′), 3.81(1H, dd, J=2.1, 12.3 Hz, H-5′), 2.14 (3H, s, acetyl), 2.13 (3H, s, acetyl), 2.11 (3H, s, acetyl).

Workup

  1. customA reaction vessel was prptected from light
  2. stirringthe resulting mixture was stirred vigorously at room temperature for 2 days
  3. washThe separated organic phase was washed with 50 mL of a 5% aqueous solution of sodium hydroxide three times
  4. dry with materialwith 50 mL of water three times, dried over anhydrous sodium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-492a9dad77ea4e85a5aad7d6a038df98
Source dataset
uspto-grants-2005_10
Patent number
US06958389B2

Reaction notes

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