Water → (R)-1-(3-Tert-butyloxycarbonylphenyl)ethylmethanesulfonyl Ether

HRID 2300771Notes

Reaction equation

HRID 2300771 reaction equation
[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([C@H:14]([OH:16])[CH3:15])[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>C(Cl)Cl>[C:1]([O:5][C:6]([C:8]1[CH:9]=[C:10]([C@H:14]([O:16][S:27]([CH3:26])(=[O:29])=[O:28])[CH3:15])[CH:11]=[CH:12][CH:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 69964056(R)-1-(3-Tert-butyloxycarbonylphenyl)ethanol

Product 1

HCID 86758754(R)-1-(3-Tert-butyloxycarbonylphenyl)ethylmethanesulfonyl EtherYield 102.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-1-(3-Tert-butyloxycarbonylphenyl)ethanol (3.28 mmol) was dissolved in CH2Cl2 (10 mL), diisopropylethylamine (4.92 mmol) added and the resultant solution cooled to 0° C. This mixture was stirred as methanesulfonyl chloride (3.94 mmol) was added dropwise. After 45 min the mixture was poured into water and extracted 3× with diethyl ether. The organic extracts were combined, washed with brine, dried (MgSO4) and concentrated under reduced pressure to yield 1.01 g of an oil which was used with out further purification. 1H NMR (500 MHz, CDCl3): δ 8.03 (m, 1H); 8.01 (m, 1H); 7.60 (m, 1H); 7.48 (t, J=7.6 Hz, 1H); 5.80 (q, J=6.6 Hz, 1H); 2.81 (s, 3H); 1.76 (d, J=6.6 Hz, 3H); 1.63 (s, 9H).

Workup

  1. additionwas added dropwise
  2. extractionextracted 3× with diethyl ether
  3. washwashed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7e75c35254aa469fbfd411a61a3fd1de
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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