Acetic Anhydride → HCID 67229404, compound

HRID 1044439Notes

Reaction equation

HRID 1044439 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][O:17][CH3:18])[CH:12]=[CH:11][C:10]=1[CH:19]=[CH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[CH:25][C:24]=1[OH:37])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:45](OC(=O)C)(=[O:47])[CH3:46]>>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([O:15][CH2:16][O:17][CH3:18])[CH:12]=[CH:11][C:10]=1[CH:19]=[CH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[CH:25][C:24]=1[O:37][C:45](=[O:47])[CH3:46])=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 67228657HCID 67228657, compound

Product 1

HCID 67229404HCID 67229404, compoundYield 92%

Conditions

Temperature
60 °C

Procedure

To a solution of 2-benzyloxy-4-methoxymethyloxy-4′-benzyloxy-2′-hydroxy-chalcone (0.496 g, 1 mmol), in 10 mL of acetic anhydride was added triethylamine (0.25 mL, 2 mmol) and the solution heated at 60° C. for ca. 6 hrs. After disappearance of starting material (TLC), the hot reaction mixture was poured into ice water:methanol (1:1) ca. 50 mL. A solid precipitated upon vigorous stirring. The solid was filtered, dried and recrystallized from methanol (ca. 15 mL) to obtain 0.495 g (92%) of white solid: mp 94-96° C.; TLC Rf0.21 in hexanes:EtOAc (3:1); 1H NMR (400 MHz, DMSO-d6) δ 7.78-7.75 (m, 2H), 7.71-7.69 (d, 1H, J=8.8 Hz, Ar—H6′), 7.49-7.36 (m, 10+1H, 2×C6H6+Ar—H8), 6.99-6.96 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5′), 6.90 (d, 1H, J=2.4 Hz, Ar—H3′), 6.85 (d, 1H, J=2 Hz, Ar—H3), 6.72-6.69 (dd, 1H, 2J=8.4 Hz, 3J=2.4 Hz, Ar—H5), 5.26 (s, 2H, O—CH2), 5.20 (s, 4H, O—CH2), 3.39 (s, 3H, OCH3), 2.18 (s, 3H, CH3CO); 13C NMR (100 MHz, DMSO-d6) δ 189, 169.5, 162.5, 160.9, 159.6, 151.4, 139.5, 137.2, 136.9, 132.3, 131.7, 129.3, 129.2, 128.8, 128.6, 128.6, 125.2, 123.3, 117.6, 113, 110.8, 109.1, 102.2, 94.5, 70.7, 70.5, 56.6, 21.5; analysis calc'd. for C33H30O7: C, 73.60; H, 5.61; O, 20.81. found: C, 73.86; H, 5.62; O, 20.79.

Workup

  1. customA solid precipitated upon vigorous stirring
  2. filtrationThe solid was filtered
  3. customdried
  4. customrecrystallized from methanol (ca. 15 mL)

Sources & evidence

ORD record
ord-577a6418911d4589936ff58073bd80e2
Source dataset
uspto-grants-2013_10
Patent number
US08563599B2

Reaction notes

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