Dibenzyl ether → 1-Adamantanol

HRID 2355803Notes

Reaction equation

HRID 2355803 reaction equation
O(CC1C=CC=CC=1)CC1C=CC=CC=1.C([O:23][C:24]12[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2)C1C=CC=CC=1>>[C:24]12([OH:23])[CH2:31][CH:30]3[CH2:29][CH:28]([CH2:27][CH:26]([CH2:32]3)[CH2:25]1)[CH2:33]2

Participants

3

Reactant 2

HCID 7657Dibenzyl etherHCID 11601197HCID 11601197, compound2×

Product 1

HCID 641521-Adamantanol

Procedure

A mixture of pyridinium triflate 1 (100 mg, 0.29 mmol), benzotrifluoride (PhCF3, 0.29 mL), MgO (11.5 mg, 0.29 mmol), and 28 (21,8 mg, 0.14 mmol) was subjected to the standard procedure to afford 0.0363 g of a yellow oil, which was determined by 1H NMR analysis to consist of 8.7 mg of Bn2O and 0.0276 g (80%) of 1-benzyloxyadamantane (3i). Spectroscopic analysis was consistent with the data reported previously for 3i.

Sources & evidence

ORD record
ord-ea19d12baff646cba0a8b3180202294c
Source dataset
uspto-grants-2010_07
Patent number
US07754909B1

Reaction notes

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