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

HRID 1734790Notes

Reaction equation

HRID 1734790 reaction equation
BrC1C=CC(O[CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)=C(C(C)(C)C)C=1.[C:19]12([C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=3[OH:36])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1C=CCCC1>ClCCl>[C:19]12([C:29]3[CH:34]=[CH:33][C:32]([Br:35])=[CH:31][C:30]=3[O:36][CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][O:10]3)[CH2:20][CH:21]3[CH2:27][CH:25]([CH2:24][CH:23]([CH2:22]3)[CH2:28]1)[CH2:26]2

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 158188564-Bromo-2-t-butyl-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 mmol) 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. PMR (CDCl3):d 1.6-2.1 (21H, m), 3.65-3.72 (1H, m), 3.8-3.93 (1H, m), 5.45 (1H, t, J=2.8 Hz), 7.04-7.08 (2H, m), 7.32 (1H, br s).

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-704b749fcf7745ef87320f192e7eeb4f
Source dataset
uspto-grants-1996_07
Patent number
US05534641

Reaction notes

Loading…