3,4-dihydro-2H-pyran → 2H-Pyran, 2-[(5-bromo-2,2-dimethylpentyl)oxy]tetrahydro-

HRID 239084Notes

Reaction equation

HRID 239084 reaction equation
BrC[CH2:3][CH2:4][CH2:5][C:6]([CH3:21])([C:15]1C=CC=CC=1)[CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1.[Br:22]CCCC(C)(C)CO.O1C=CCCC1>C(Cl)Cl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:22][CH2:3][CH2:4][CH2:5][C:6]([CH3:21])([CH3:15])[CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 111831775-Bromo-2,2-dimethylpentan-1-olHCID 112104532-(6-Bromo-2-methyl-2-phenylhexyloxy)-tetrahydropyran

Product 1

HCID 117375402H-Pyran, 2-[(5-bromo-2,2-dimethylpentyl)oxy]tetrahydro-Yield 90%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

According to the procedure for the preparation of 207d, 206a (78.0 g, 0.40 mol) was reacted with 3,4-dihydro-2H-pyran (41.5 g, 0.49 mol) and p-toluenesulfonic acid hydrate (0.42 g, 2.2 mmol) in CH2Cl2 (0.5 L) to yield 207a (101.0 g, 90%) as a pale-yellow oil, which was used without further purification. 1H NMR (CDCl3): δ 4.55 (t, 1 H, J=2.9), 3.83 (m, 1 H), 3.51 (m, 1 H), 3.47 (d, 1 H, J=9.0), 3.38 (t, 2 H, J=6.8), 2.98 (d, 1 H, J=9.0), 1.94-1.75 (m, 2 H), 1.75-1.44 (m, 6 H), 1.40 (t, 2 H, J=8.5), 0.91 (s, 3 H), 0.90 (s, 3 H). 13C NMR (CDCl3): δ 99.01, 76.17, 61.85, 37.89, 34.66, 34.04, 30.62, 27.92, 25.60, 24.64, 24.56, 19.41. HRMS (LSIMS, nba): Calcd for C12H24BrO2 (MH+): 279.0960, found: 279.0955.

Sources & evidence

ORD record
ord-a65dedb59c394ab3a96133f6d289a5a2
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

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