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

HRID 1440505Notes

Reaction equation

HRID 1440505 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)=[C:4]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:3]=1.[C:19]12(C3C=CC(Br)=CC=3O)[CH2:28][CH:23]3CC(C[CH:21]([CH2:22]3)[CH2:20]1)C2.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O1C=CCCC1>ClCCl>[C:15]12([C:4]3[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=3[O:8][CH:9]3[CH2:14][CH2:13][CH2:12][CH2:11][O:10]3)[CH2:18][CH:21]3[CH2:22][CH:23]([CH2:28][CH:19]([CH2:20]3)[CH2:16]1)[CH2:17]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 221045702-(1-Adamantyl)-4-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 9.17 g (29.9 mmol) of 2-(1-adamantyl)-4-bromophenol (Compound F), 0.75 g (3.0 mmol) of pyridinium p-toluenesulfonate, 3.77 g (4.1 ml, 44.8 mmol) of 3,4-dihydro-2H-pyran and 50 ml of dichloromethane produced a bright yellow solid. Purification by flash chromatography (preabsorbed onto silica with chloroform, eluted with 2% ethyl acetate in hexane) yielded the title compound as a nearly white solid. PMR (CDCl3): d 1.6-2.2 (21H, m), 3.6-3.7 (1H, m), 3.8-3.9 (1H, m), 5.43 (1H, t, J=2.4 Hz), 7.05 (1H, d, J=8.7 Hz), 7.23 (1H, dd, J=8.7, 2.5 Hz), 7.30 (1H, d, J=2.5 Hz).

Workup

  1. customproduced a bright yellow solid
  2. customPurification
  3. customby flash chromatography (preabsorbed onto silica with chloroform, eluted with 2% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f30caf015a19456da5173b4c36084aa6
Source dataset
uspto-grants-1996_03
Patent number
US05498795

Reaction notes

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