Benzyl mercaptan → 3-Benzylsulfanyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid ethyl ester

HRID 1796140Notes

Reaction equation

HRID 1796140 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5]([CH2:7][O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[CH2:6])[CH3:2].C([O-])(O)=O.[Na+].[CH2:21]([SH:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C.O>[CH2:1]([O:3][C:4](=[O:15])[CH:5]([CH2:7][O:8][CH:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)[CH2:6][S:28][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH3:2]

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 516892Sodium BicarbonateHCID 210257162-(Tetrahydro-pyran-4-yloxymethyl)-acrylic acid ethyl ester

Product 1

HCID 694384543-Benzylsulfanyl-2-(tetrahydro-pyran-4-yloxymethyl)-propionic acid ethyl esterYield 36.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A suspension of 2-(tetrahydro-pyran-4-yloxymethyl)-acrylic acid ethyl ester (2.2 g, 10.2 mmol) in ethanol (100 ml) was treated with a solution of NaHCO3 (0.86 g, 10.2 mmol) in water ml (10 ml) and benzyl mercaptan (1.21 ml, 10.2 mmol) at room temperature overnight. Ethanol evaporated off under reduced pressure, crude partitioned between ethyl acetate and water, organic layer separated and purified by mplc eluting with 1:9 to 2:8 v/v ethyl acetate-heptane mixture to give the title compound as pale yellow oil (1.27 g). MS: 339 (MH+); LCMS (Protocol B) retention time 4.3 minutes.

Workup

  1. customEthanol evaporated off under reduced pressure, crude
  2. custompartitioned between ethyl acetate and water, organic layer
  3. customseparated
  4. custompurified
  5. washby mplc eluting with 1:9 to 2:8 v/v ethyl acetate-heptane mixture

Sources & evidence

ORD record
ord-d8812ce882d7483cbcd6dbb7c2a19dc8
Source dataset
uspto-grants-2006_04
Patent number
US07030116B2

Reaction notes

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