Ethanol → HCID 18784746, compound

HRID 1108526Notes

Reaction equation

HRID 1108526 reaction equation
Cl.[C:2]1([C:8](C2C=CC=CC=2)=[CH:9][CH2:10][N:11]2[CH2:16][CH2:15][CH:14]([N:17]3[CH2:25][C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]3=[O:26])[CH2:13][CH2:12]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([OH:35])C>>[O:35]=[C:8]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][CH:14]([N:17]2[CH2:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]2=[O:26])[CH2:13][CH2:12]1

Participants

3

Reactant 2

HCID 702Ethanol2×HCID 131720603HCID 131720603, compound

Product 1

HCID 18784746HCID 18784746, compoundYield 37%

Procedure

To a solution of Example 2 Part A compound (1.93 g, 8.92 mmol) in dry ethanol (15 mL) at RT was added a solution of Part B compound (1.1 g, 7.43 mmol) in dry ethanol (2 mL). The reaction was stirred at RT for 4 h. The reaction was evaporated to dryness. Ethyl ether (150 mL) was added, and the solution was washed water (2×30 mL), brine (2×30 mL) and dried over MgSO4. Purification was performed by flash chromatography on silica gel (150 g), loaded and eluted with 4% methanol in dichloromethane. Pure fractions were combined and evaporated to give title compound (1.0 g, 37%) as a yellowish solid.

Workup

  1. customThe reaction was evaporated to dryness
  2. additionEthyl ether (150 mL) was added
  3. washthe solution was washed water (2×30 mL), brine (2×30 mL)
  4. dry with materialdried over MgSO4
  5. customPurification
  6. washeluted with 4% methanol in dichloromethane
  7. customevaporated

Sources & evidence

ORD record
ord-a737b8f231724848b4eb009bd56d89b0
Source dataset
uspto-grants-2000_05
Patent number
US06066650

Reaction notes

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