Hydrochloric Acid → HCID 11393125, compound

HRID 431745Notes

Reaction equation

HRID 431745 reaction equation
CC(C[AlH]CC(C)C)C.[CH2:10]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][C:29](OCC)=[O:30])=[C:20]([N+:34]([O-:36])=[O:35])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.N#N.Cl>C1COCC1>[CH2:10]([O:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([CH2:28][CH2:29][OH:30])=[C:20]([N+:34]([O-:36])=[O:35])[CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 947NitrogenHCID 14487Diisobutylaluminum hydrideHCID 11222306Ethyl 2-[4-benzyloxy-2-nitronaphthalen-1-yl]acetate

Product 1

HCID 11393125HCID 11393125, compoundYield 106.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIBAL-H (1.0 M, 3.84 mL, 3.84 mmol) was added to a solution of ethyl 2-[4-benzyloxy-2-nitronaphthalen-1-yl]acetate (0.35 g, 0.96 mmol) in THF (4 mL) slowly under N2 atmosphere at 0° C., and stirred for 15 min. The mixture was poured into chilled 1 N HCl (10 mL) slowly, and the mixture was extracted with AcOEt (50 mL). The organic layer was washed with 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL), and then the organic layer was dried (Na2SO4) and evaporated to yield 2-[4-benzyloxy-2-nitronaphthalen-1-yl]ethanol (0.33 g, quant.) as a dark brown solid. Mp 82-90 ° C.; 1H NMR (CDCl3, 500 MHz) δ 8.43 (d, 8.5, 1H), 8.25 (d, 9.0, 1H), 7.71 (t, 7.0, 1H), 7.65 (t, 7.0, 1H), 7.54 (d, 8.0, 2H), 7.45 (t, 7.5, 2H), 7.40 (t, 7.0, 1H), 7.19 (s, 1H), 5.29 (s, 2H), 4.08 (t, 6.5, 2H), 3.49 (t, 6.5, 2H); EIMS m/z 323 (M+); IR (neat) νmax 3368, 2929, 1593, 1526, 1513, 1463, 1423, 1363, 1337, 1271, 1240, 1161, 1103, 1039, 829, 755, 697 cm−1.

Workup

  1. additionThe mixture was poured
  2. extractionthe mixture was extracted with AcOEt (50 mL)
  3. washThe organic layer was washed with 1 M HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and saturated aqueous NaCl (10 mL)
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-1fc44dde40064d16be860f8baafec083
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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