1-Pentanol → HCID 69086263, compound

HRID 1427172Notes

Reaction equation

HRID 1427172 reaction equation
[CH2:1](O)[CH2:2][CH2:3][CH2:4][CH3:5].CC([OH:12])CCC.[Cl-].C(N(CC)CC)C.[CH3:21][C:22]1[CH:35]=[C:34]2[C:25]([S:26][C:27]3[CH:28]=[C:29]([C:37](Cl)=[O:38])[CH:30]=[CH:31][C:32]=3[C:33]2=[O:36])=[CH:24][CH:23]=1>O.C(Cl)Cl>[CH3:21][C:22]1[CH:35]=[C:34]2[C:25]([S:26][C:27]3[CH:28]=[C:29]([C:37]([O:38][CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[O:12])[CH:30]=[CH:31][C:32]=3[C:33]2=[O:36])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 62761-PentanolHCID 223862-PentanolHCID 108509407-methyl-9-oxo-thioxanthene-3-carbonyl ChlorideHCID 22292735HCID 22292735, compound

Product 1

HCID 69086263HCID 69086263, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1.0 g (11.36 mmoles) of pentan-1-ol (containing also -pentan-2-ol) and 1.0 g (9.90 mmoles) of triethyl amine chloride are added to the CH2Cl2 solution containing 2.26 g (7.41 mmoles) of 7-methyl-9-oxo-thioxanthene-3-carbonyl chloride. After approximately 1 hour at room temperature under stirring, the mixture is poured in water, the organic phase is separated and washed again with water. The organic phase is then separated, dehydrated and after purification on a flash column (SiO2— eluent: CH2Cl2:AcOEt 8:2) it is dried, obtaining 1.74 g (71.6%) of a yellow solid with the following spectral properties:

Workup

  1. customthe organic phase is separated
  2. washwashed again with water
  3. customThe organic phase is then separated
  4. customafter purification on a flash column (SiO2— eluent: CH2Cl2:AcOEt 8:2) it
  5. customis dried

Sources & evidence

ORD record
ord-1de5f6261a3f47b98d1680ba0f77c100
Source dataset
uspto-grants-2015_01
Patent number
US08933142B2

Reaction notes

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