Water → HCID 10778954, compound

HRID 2260396Notes

Reaction equation

HRID 2260396 reaction equation
C([O:4][CH2:5][C:6]1[CH:19]=[C:18]2[C:9]([C:10](=[O:21])[C:11]3[C:16]([C:17]2=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:8]2[CH2:22][CH2:23][CH2:24][C:7]=12)(=O)C.O.C(N(CC)CC)C>CO>[OH:4][CH2:5][C:6]1[CH:19]=[C:18]2[C:9]([C:10](=[O:21])[C:11]3[C:16]([C:17]2=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=3)=[C:8]2[CH2:22][CH2:23][CH2:24][C:7]=12

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 19000639HCID 19000639, compound

Product 1

HCID 10778954HCID 10778954, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
55 °C

Procedure

A mixture of 2,3-dihydro-4-acetoxymethyl-1H-cyclopent[a]anthracene-6,11-dione (74 mg, 0.23 mmol) in MeOH (12 mL) containing H2O (3mL) and triethylamine (2mL) is heated at 55° C. for 3 hours. The mixture is evaporated in vacuo, and the residue is coevaporated twice with EtOH (10 mL) to dryness. The residue is recrystallized from CHCl3 to give2,3-dihydro-4-hydroxymethyl-1H-cyclopent[a]anthracene-6,11-dione, 48 mg (75%), mp 191°-192° C. 1H NMR (DMSO-d6): δ2.14 (2H, q, J=7.6 Hz, CH2 -2), 2.88 (2H, t, J=7.6 Hz, CH2 -3), 3.40 (2H, t, J=7.6 Hz, CH2 -1), 4.61 (2H, d, J=5.5 Hz, CH2 --OH), 5.53 (1 H, t, J=5.5 Hz, OH), 7.90-8.18 (5H, m, Ar--H). Anal. Calc'd for C18H14O3 : C, 77.68; H, 5.07. Found: C, 77.70; H, 5.06.

Workup

  1. customThe mixture is evaporated in vacuo
  2. customThe residue is recrystallized from CHCl3 to give2,3-dihydro-4-hydroxymethyl-1H-cyclopent[a]anthracene-6,11-dione, 48 mg (75%), mp 191°-192° C

Sources & evidence

ORD record
ord-fc73ee851f4445fabe3e55bdd7077220
Source dataset
uspto-grants-1995_12
Patent number
US05476952

Reaction notes

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