4-Toluenesulfonyl chloride → (+/-)-(7-Nitro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate

HRID 2116074Notes

Reaction equation

HRID 2116074 reaction equation
[N+:1]([C:4]1[C:12]2[O:11][CH:10]([CH2:13][OH:14])[CH2:9][C:8]=2[CH:7]=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(C(C)C)CC)(C)C.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>ClCCl>[CH3:34][C:24]1[CH:29]=[CH:28][C:27]([S:30]([O:14][CH2:13][CH:10]2[CH2:9][C:8]3[CH:7]=[CH:6][CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[C:12]=3[O:11]2)(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11063317(+/-)-(7-Nitro-2,3-dihydro-1-benzofuran-2-yl)methanol

Product 1

HCID 86599155(+/-)-(7-Nitro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (±)-(7-nitro-2,3-dihydro-1-benzofuran-2-yl)methanol (3.14 g, 16.09 mol) in dichloromethane (100 mL) was added diisopropylethyl amine (4.16 g, 32.18 mmol), N,N-dimethylaminopyridine (0.39 g, 3.2 mmol), and p-toluenesulfonyl chloride (4.6 g, 24.13 mmol) the reaction was allowed to stir at room temperature for 12 h. The reaction was diluted with dichloromethane (500 mL), washed with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous sodium chloride (200 mL), dried (magnesium sulfate) and the solvent removed in vacuo to give a crude oil. Purification by flash column chromatography (silica, dichloromethane: hexanes 3:10) afforded 5.2 g (94%) of (±)-(7-nitro-2,3-dihydro-1-benzofuran-2-yl)methyl 4-methylbenzenesulfonate as off-white solid. mp 129-131° C.

Workup

  1. washwashed with saturated aqueous sodium bicarbonate (200 mL), saturated aqueous sodium chloride (200 mL)
  2. dry with materialdried (magnesium sulfate)
  3. customthe solvent removed in vacuo
  4. customto give a crude oil
  5. customPurification by flash column chromatography (silica, dichloromethane: hexanes 3:10)

Sources & evidence

ORD record
ord-423c347516624bbfa48f9d5e2c0b7b91
Source dataset
uspto-grants-2008_10
Patent number
US07435837B2

Reaction notes

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