3,4-dihydro-2H-pyran → 2-(7-Bromo-2-methyl-2-phenylheptyloxy)-tetrahydropyran

HRID 239088Notes

Reaction equation

HRID 239088 reaction equation
Br[CH2:2][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][CH2:23]CCCCC(C)(C1C=CC=CC=1)CO.O1C=CCCC1>O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:22][CH2:23][CH2:2][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

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 112104532-(6-Bromo-2-methyl-2-phenylhexyloxy)-tetrahydropyranHCID 113006147-Bromo-2-methyl-2-phenylheptan-1-ol

Product 1

HCID 113830712-(7-Bromo-2-methyl-2-phenylheptyloxy)-tetrahydropyranYield 76%

Reagents, catalysts & solvents 1

HCID 521998p-Toluenesulfonic acid monohydrateCatalyst

Procedure

According to the method described for the synthesis of 207d, 206h (51.0 g, 179 mmol) was reacted with 3,4-dihydro-2H-pyran (18.80 g, 223 mmol) and p-toluenesulfonic acid hydrate (1.21 g, 6.36 mmol). Filtration through aluminum oxide (370 g) and concentration in vacuo afforded 207h (48.75 g, 76%) as a yellowish oil. 1H NMR (CDCl3): δ 7.35-7.17 (m, 10 H), 4.53 (m, 1 H), 4.49 (m, 1 H), 3.82 (m, 2 H), 3.79 (m, 1 H), 3.68-3.60 (m, 2 H), 3.45-3.35 (m, 2 H), 3.32 (t, 4 H, J=6.9), 1.82-1.18 (m, 28 H), 1.35 (s, 6 H). 13C NMR (CDCl3): δ 146.12, 128.11, 126.66, 125.89, 99.18, 99.04, 76.46, 62.02, 61.83, 42.17, 42.07, 38.91, 38.73, 34.12, 32.80, 30.70, 29.04, 25.66, 23.33, 22.97, 22.89, 19.49, 19.39. HRMS (LSIMS, nba): Calcd for C19H30BrO2 (MH+): 369.1429, found: 369.1430.

Workup

  1. filtrationFiltration
  2. concentrationthrough aluminum oxide (370 g) and concentration in vacuo

Sources & evidence

ORD record
ord-f385f266edd4414aa65952b69fa0055c
Source dataset
uspto-grants-2014_02
Patent number
US08642653B2

Reaction notes

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