Methanol → HCID 69472233, compound

HRID 1180454Notes

Reaction equation

HRID 1180454 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:9][CH:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]([O:13]C)=[O:12])=[CH:4][CH:3]=1.O1CCCC1.CO.[Li]>Cl.ClCCl.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[S:9][CH:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 3028194LithiumHCID 69472984HCID 69472984, compound

Product 1

HCID 69472233HCID 69472233, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1 g (2.4 mmoles) of methyl 2-{[(4-bromophenyl)(phenyl)methyl]thio}-4-methylpentanoate from example 73 step 2 in a ternary mixture of tetrahydrofuran, methanol and water was added solid lithium hydroxyde monohydrate (151 mg, 3.6 mmoles). The reaction was stirred until disappearance of the starting material by thin layer chromatography and diluted with 1N hydrochloric acid and dichloromethane. The phases were separated and the aqueous phase was washed twice with dichloromethane. The combined organic layers were dried over magnesium sulfate and concentrated under reduced pressure. The title acid was used without further purification.

Workup

  1. customThe phases were separated
  2. washthe aqueous phase was washed twice with dichloromethane
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe title acid was used without further purification

Sources & evidence

ORD record
ord-2794677bdcb149cb955221ef05c1484e
Source dataset
uspto-grants-2007_10
Patent number
US07279478B2

Reaction notes

Loading…