Tetrahydrofuran → HCID 12333721, compound

HRID 475862Notes

Reaction equation

HRID 475862 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.C1COCC1.[CH:16]12[O:21][CH:20]1[CH2:19][CH2:18][CH2:17]2.[NH4+].[Cl-]>[Cu]I>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:19]1[CH2:18][CH2:17][CH2:16][CH:20]1[OH:21]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 92446-Oxabicyclo[3.1.0]hexaneHCID 25517Ammonium ChlorideHCID 178489560HCID 178489560, compound

Product 1

HCID 12333721HCID 12333721, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

To a solution of (2-methoxyphenyl)magnesium bromide in THF (47.4 ml, 47.4 mmol) was added Copper(I) iodide (0.632 g, 3.32 mmol). The resulting solution was stirred at RT for 10 min. 6-oxabicyclo[3.1.0]hexane (4.11 ml, 47.4 mmol) was slowly added and the reaction mixture was stirred at RT overnight. Sat. NH4Cl was slowly added and the mixture was stirred at RT for 30 min. The product was extracted with CH2Cl2. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex) to get 2-(2-methoxyphenyl)cyclopentanol (9.03 g, 47.0 mmol, 99% yield). LC-MS (M+Na)+=215.1. 1H NMR (500 MHz, CDCl3) δ 7.21 (t, J=5.8 Hz, 2H), 6.97 (t, J=7.3 Hz, 1H), 6.88 (d, J=8.2 Hz, 1H), 4.24 (q, J=5.9 Hz, 1H), 3.79 (s, 3H), 3.38-3.27 (m, 2H), 2.23-2.10 (m, 1H), 2.09-1.97 (m, 1H), 1.95-1.85 (m, 1H), 1.85-1.71 (m, 3H).

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. stirringthe mixture was stirred at RT for 30 min
  3. extractionThe product was extracted with CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (SG, 0% to 60% EtOAc/Hex)

Sources & evidence

ORD record
ord-86038715a39844fb8c6525f05c8682f5
Source dataset
uspto-grants-2014_01
Patent number
US08637525B2

Reaction notes

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