Triphenylphosphine → t-butyl (R)-4-(2-acetyl-5-(3-pyridylmethoxy)phenoxy)-4-(2-methylphenyl)butanoate

HRID 322989Notes

Reaction equation

HRID 322989 reaction equation
N(C(OC(C)C)=O)=NC(OC(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:34]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]2[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=2)=[CH:39][C:38]=1[OH:51])(=[O:36])[CH3:35].O[C@H:53]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1[CH3:69])[CH2:54][CH2:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57]>C1COCC1>[C:34]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]2[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=2)=[CH:39][C:38]=1[O:51][C@@H:53]([C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][C:64]=1[CH3:69])[CH2:54][CH2:55][C:56]([O:58][C:59]([CH3:62])([CH3:61])[CH3:60])=[O:57])(=[O:36])[CH3:35]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 10705824tert-butyl (S)-4-hydroxy-4-(2-methylphenyl)butanoateHCID 167367812-Acetyl-5-(3-pyridylmethoxy)phenol

Product 1

HCID 53975835t-butyl (R)-4-(2-acetyl-5-(3-pyridylmethoxy)phenoxy)-4-(2-methylphenyl)butanoateYield 22.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropyl azodicarboxylate (8 g) is added portionwise to a stirred solution of triphenylphosphine (10.5 g) in THF (100 mL) at 0° C. under nitrogen. Stirring is continued at 0° C. for 15 minutes. A solution of 2-acetyl-5-(3-pyridylmethoxy)phenol (4.5 g) and tert-butyl (S)-4-hydroxy-4-(2-methylphenyl)butanoate (4.9 g) in THF (100 mL) is added at such a rate that the temperature does not exceed 5° C. The reaction is allowed to warm to ambient temperature stirred for 16 hours, then concentrated in vacuo. The residue is partitioned between ethyl acetate (200 mL) and water (200 mL) and the organic phase dried over magnesium sulphate, filtered and concentrated in vacuo.The residue is purified by flash chromatography on silica eluting initially with a mixture of ethyl acetate and cyclohexane (1:1 v/v) then with ethyl acetate. Fractions homogeneous in the required product are combined and evaporated to give t-butyl (R)-4-(2-acetyl-5-(3-pyridylmethoxy)phenoxy)-4-(2-methylphenyl)butanoate (2 g).

Workup

  1. customdoes not exceed 5° C
  2. stirringstirred for 16 hours
  3. concentrationconcentrated in vacuo
  4. customThe residue is partitioned between ethyl acetate (200 mL) and water (200 mL)
  5. dry with materialthe organic phase dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo.The residue
  8. customis purified by flash chromatography on silica eluting initially with a mixture of ethyl acetate and cyclohexane (1:1 v/v)
  9. customevaporated

Sources & evidence

ORD record
ord-8546cd1c87444010aa3d6fb0f3952cae
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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