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Imidazole → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methyliodide

HRID 860546
Notes
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Reaction equation

HRID 860546 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]([CH2:29]O)[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.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1.[I:55]I>C1COCC1.CCOC(C)=O>[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][I:55])[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 103408316-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylalcohol

Product 1

HCID 695838266-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methyliodideYield 45%

Reagents, catalysts & solvents 2

HCID 8028
Tetrahydrofuran
Solvent
2×
HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-[3-(1-adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methyl alcohol (0.365 g, 0.92 mmol), triphenylphosphine (0.366 g, 1.39 mmol) and imidazole (0.095 g, 1.39 mmol) in 7 mL of anhydrous THF at 0° C. was added dropwise a solution of I2 (0.303 g, 1.19 mmol) in 4 mL of anhydrous THF. After 30 minutes the mixture was diluted with EtOAc and washed with sodium thiosulfate aq. (100 mL), brine (100 mL), dried with magnesium sulfate, filtered and evaporated. The residue was purified on silica gel (eluent: hexane:EtOAc 100 to 95:5) to give 0.210 g of 6-[3-(1-adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methyliodide (45%). 1H NMR (300 MHz; CDCl3): δ 1.80 (s, 6H), 2.10–2.18 (m, 9H), 3.89 (s, 3H), 4.65 (s, 2H), 6.98 (d, J=8.7 Hz, 1H), 7.46–7.57 (m, 3H), 7.71–7.93(m, 5H).

Workup

  1. washwashed with sodium thiosulfate aq. (100 mL), brine (100 mL)
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified on silica gel (eluent: hexane:EtOAc 100 to 95:5)

Sources & evidence

ORD record
ord-0a59f5e307f541f6b8306e8943eab9c5
Source dataset
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07153875B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes