3,4-dihydro-2H-pyran → 2-(1-Adamantyl)-5-bromo-1-(2-tetrahydropyranoxy)benzene

HRID 1940231Notes

Reaction equation

HRID 1940231 reaction equation
C(C1C=CC=CC=1O[CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][O:13]1)CCC.[C:18]12([C:28]3[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:29]=3[OH:35])[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1C=CCCC1>ClCCl>[C:18]12([C:28]3[CH:33]=[CH:32][C:31]([Br:34])=[CH:30][C:29]=3[O:35][CH:12]3[CH2:17][CH2:16][CH2:15][CH2:14][O:13]3)[CH2:19][CH:20]3[CH2:26][CH:24]([CH2:23][CH:22]([CH2:21]3)[CH2:27]1)[CH2:25]2

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19705852Butyl-1-(2-tetrahydropyranoxy)benzene2×HCID 223478532-(1-Adamantyl)-5-bromophenol2×

Product 1

HCID 221045742-(1-Adamantyl)-5-bromo-1-(2-tetrahydropyranoxy)benzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the same general procedure as for the preparation of of 4-bromo-2-t-butyl-1-(2-tetrahydropyranoxy)benzene (Compound H), but instead using 12.56 g (40.9 mmol) of 2-(1-adamantyl)-5-bromophenol (Compound G), 1.03 g (4.1 nunol) of pyridinium p-toluenesulfonate, 5.16 g (5.6 ml, 61.3 mmol) of 3,4-dihydro-2H-pyran and 50 ml of dichloromethane produced a clear, orange solution. During aqueous workup, the organic phase was washed with 3×150 ml-portions of sat. aqueous NaHCO3 solution to produce a light yellow solid. Purification by flash chromatography (silica, 3% ethyl acetate in hexane) yielded the title compound as a white solid.

Workup

  1. customproduced a clear, orange solution
  2. washDuring aqueous workup, the organic phase was washed with 3×150 ml-portions of sat. aqueous NaHCO3 solution
  3. customto produce a light yellow solid
  4. customPurification by flash chromatography (silica, 3% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-48b51be7569242e8984374fe716b8ee9
Source dataset
uspto-grants-1997_12
Patent number
US05698700

Reaction notes

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