HCID 10908531, compound → HCID 10930203, compound

HRID 1601884Notes

Reaction equation

HRID 1601884 reaction equation
[CH:1]1[C:17]2[C:5](=[C:6]3[CH:51]=[CH:50][CH:49]=[CH:48][C:7]3=[C:8]3[C:16]=2[CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:39]=[CH:38][C:32]([C:33](OCC)=[O:34])=[CH:31][CH:30]=2)[C:14]2[C:9]3=[C:10]3[CH:47]=[CH:46][CH:45]=[CH:44][C:11]3=[C:12]3[CH:43]=[CH:42][CH:41]=[CH:40][C:13]3=2)[CH:4]=[CH:3][CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C>C1COCC1>[CH:40]1[C:13]2[C:12](=[C:11]3[CH:44]=[CH:45][CH:46]=[CH:47][C:10]3=[C:9]3[C:14]=2[CH:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][O:28][C:29]2[CH:30]=[CH:31][C:32]([CH2:33][OH:34])=[CH:38][CH:39]=2)[C:16]2[C:8]3=[C:7]3[CH:48]=[CH:49][CH:50]=[CH:51][C:6]3=[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:17]3=2)[CH:43]=[CH:42][CH:41]=1

Participants

4

Reactant 2

HCID 10908531HCID 10908531, compoundHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 10930203HCID 10930203, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-[[10-(17H-tetrabenzo[a,c,g,i]fluoren-17-yl)decyl]oxy]benzoate (9) (2.03 g, 3.03 mmol) was charged to an oven-dried flask along with freshly distilled THF (40 mL) and the resultant solution stirred at room temperature under an atmosphere of nitrogen. Diisobutyl aluminum hydride (12.0 mL, 12.00 mmol) was added via syringe and the resulting mixture stirred at room temperature under nitrogen for 2 hours, after which time, TLC analysis showed that all the starting material had been consumed. The reaction was quenched with the addition of HCl (2 M, 40 mL), and the organic products were extracted with ethyl acetate (3×50 mL), washed with saturated Na2CO3 (40 mL) and water (40 mL), and dried over MgSO4. Excess solvent was removed in vacuo to yield 4-[[10-(17H-tetrabenzo[a,c,g,i]fluoren-17-yl)decyl]oxy]-benzenemethanol (1.7765 g, 2.82 mmol, 94%).

Workup

  1. customhad been consumed
  2. customThe reaction was quenched with the addition of HCl (2 M, 40 mL)
  3. extractionthe organic products were extracted with ethyl acetate (3×50 mL)
  4. washwashed with saturated Na2CO3 (40 mL) and water (40 mL)
  5. dry with materialdried over MgSO4
  6. customExcess solvent was removed in vacuo

Sources & evidence

ORD record
ord-fb9ad95abe2e4c12933f1689286e6cd6
Source dataset
uspto-grants-1999_11
Patent number
US05977400

Reaction notes

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