Diisobutylaluminum hydride → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylalcohol

HRID 860547Notes

Reaction equation

HRID 860547 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH:29]=[O:30])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:1]12([C:11]3[CH:12]=[C:13]([C:19]4[CH:20]=[C:21]5[C:26](=[CH:27][CH:28]=4)[CH:25]=[C:24]([CH2:29][OH:30])[CH:23]=[CH:22]5)[CH:14]=[CH:15][C:16]=3[O:17][CH3:18])[CH2:8][CH:7]3[CH2:6][CH:5]([CH2:4][CH:3]([CH2:9]3)[CH2:2]1)[CH2:10]2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 865860366-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthaldehyde

Product 1

HCID 103408316-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylalcoholYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthaldehyde (0.500 g, 1.26 mmol, see Example 9) in 15 mL toluene at −78° C. under an atmosphere of argon was added DIBAL (2.5 mL, 1.0 M in toluene, 3.79 mmol) via needle dropwise. After 1 hour the reaction mixture was quenched with ethyl acetate and the resulting mixture was allowed to warm to RT. The mixture was diluted with ethyl acetate and washed with 1.0 N HCl, water and brine. The organics were dried with magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: CH2Cl2) to give 0.450 g of 6-[3-(1-adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylalcohol (90%), mp 169–171° C. 1HNMR (300 MHz; CDCl3): δ 1.80 (s, 6H), 2.10–2.18 (m, 9H), 3.90 (s, 3H), 4.86 (s, 2H), 6.98 (d, J=8.4 Hz, 1H), 7.24–7.25 (m, 1H), 7.46–7.59 (m, 3H), 7.71–7.74 (m, 1H), 7.80–7.89 (m, 3H), 7.97 (s, 1H).

Workup

  1. customAfter 1 hour the reaction mixture was quenched with ethyl acetate
  2. additionThe mixture was diluted with ethyl acetate
  3. washwashed with 1.0 N HCl, water and brine
  4. dry with materialThe organics were dried with magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on silica gel (eluent: CH2Cl2)

Sources & evidence

ORD record
ord-d296fb663e164309afa68a93ebca961f
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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