4-Toluenesulfonyl chloride → (3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonate

HRID 527195Notes

Reaction equation

HRID 527195 reaction equation
[CH2:1]([C:3]1([CH2:7][OH:8])[CH2:6][O:5][CH2:4]1)[CH3:2].[S:9](Cl)([C:12]1[CH:18]=[CH:17][C:15]([CH3:16])=[CH:14][CH:13]=1)(=[O:11])=[O:10].CCN(CC)CC>CN(C1C=CN=CC=1)C>[CH3:16][C:15]1[CH:17]=[CH:18][C:12]([S:9]([O:8][CH2:7][C:3]2([CH2:1][CH3:2])[CH2:6][O:5][CH2:4]2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 76444Oxt-101

Product 1

HCID 11425703(3-Ethyloxetan-3-yl)methyl 4-methylbenzenesulfonateYield 91%

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

This compound was synthesized as a colorless oil from (3-ethyloxetan-3-yl)methanol (122.4 mg, 1.05 mmol), TsCl (261.2 mg, 1.37 mmol), Et3N (159.4 mg, 1.58 mmol), and DMAP (128.8 mg, 1.05 mmol) in 91% yield by following general procedure 1.1: 1H NMR (400 MHz, CDCl3, δH) 7.80 (d, J=8.3 Hz, 2H), 7.36 (d, J=8.0 Hz, 2H), 4.35 (d, J=6.3 Hz, 2H), 4.29 (d, J=6.3 Hz, 2H), 4.15 (s, 2H), 2.45 (s, 3H), 1.73 (q, J=7.5 Hz, 2H), 0.79 (t, J=7.5 Hz, 3H); 13C NMR (100 MHz, CDCl3, OH) 145.35, 132.72, 130.21, 128.18, 71.97, 42.99, 26.26, 21.90, 8.05. ESI-MS: 271.1 (M+H+), 293.1 (M+Na+).

Sources & evidence

ORD record
ord-10e3da35a50c46e69cb3a03ecb9eb894
Source dataset
uspto-grants-2016_05
Patent number
US09346791B2

Reaction notes

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