3,4-dihydro-2H-pyran → 2-(5-Bromo-2-methyl-2-phenylpentyloxy)-tetrahydropyran

HRID 239085

Reaction equation

HRID 239085 reaction equation
BrC[CH2:3][CH2:4][CH2:5][C:6]([CH3:21])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:7][O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1.[Br:22]CCCC(C)(C1C=CC=CC=1)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])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[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 112104532-(6-Bromo-2-methyl-2-phenylhexyloxy)-tetrahydropyranHCID 113458925-Bromo-2-methyl-2-phenylpentan-1-ol

Product 1

HCID 114846082-(5-Bromo-2-methyl-2-phenylpentyloxy)-tetrahydropyranYield 95%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

According to the method described for the synthesis of 207d, 206b (20.0 g, 77.8 mmol) was treated with 3,4-dihydro-2H-pyran (8.2 g, 96.5 mmol) and p-toluenesulfonic acid hydrate (0.57 g, 3.0 mmol) in CH2Cl2 (350 mL) to afford 207b (25.2 g, 95%) as an oil, which was used without further purification. 1H NMR (CDCl3): 7.26-7.08 (m, 5 H), 4.45 (m, 1 H), 3.72 (m, 1 H), 3.58 (m, 1 H), 3.35-3.05 (m, 2 H), 3.28 (t, 2 H, J=6.6), 1.95-1.39 (m, 10 H), 1.25 (s, 3 H). 13C NMR (CDCl3): δ 145.38, 128.15, 126.51, 126.03, 99.06, 98.92, 76.20, 61.91, 61.80, 41.82, 41.74, 37.58, 37.43, 34.65, 30.61, 27.88, 25.58, 23.03, 22.90, 19.39, 19.32. HRMS (LSIMS, nba): Calcd for C17H26O2Br (MH+): 341.1116, found: 341.1127.

Sources & evidence

ORD record
ord-67f114da9bb64f9c9e02cedf7ed3abad
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Linked notes

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