Allyl Alcohol → HCID 69359289, compound

HRID 852578Notes

Reaction equation

HRID 852578 reaction equation
[CH2:1]([S:5]([NH:8][C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][CH2:20][CH3:21])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:7])=[O:6])[CH2:2][CH:3]=[CH2:4].[CH2:22](O)[CH:23]=[CH2:24].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1>[CH2:1]([S:5]([N:8]([CH2:24][CH:23]=[CH2:22])[C:9]1[CH:10]=[C:11]([CH:16]=[C:17]([CH2:19][CH2:20][CH3:21])[CH:18]=1)[C:12]([O:14][CH3:15])=[O:13])(=[O:7])=[O:6])[CH2:2][CH:3]=[CH2:4]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 69358377HCID 69358377, compound

Product 1

HCID 69359289HCID 69359289, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 3-[(3-buten-1-ylsulfonyl)amino]-5-propylbenzoate (D134) (1.3 g, 4.2 mmol, 1 equiv), 2-propen-1-ol (280 μl, 4.2 mmol, 1 equiv) and triphenylphosphine (1.28 g, 4.9 mmol, 1.15 equiv) in toluene (20 ml) at room temperature was slowly added diisopropyl azodicarboxylate (964 ml, 4.9 mmol, 1.15 equiv). The resulting solution was stirred at this temperature for 30 min then concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 4:1) gave methyl 3-[(3-buten-1-ylsulfonyl)(2-propen-1-yl)amino]-5-propylbenzoate (D135) (1.1 g, 75%) as a yellow oil. [M+H]+=352.1, RT=3.63 min.

Workup

  1. customat room temperature
  2. concentrationthen concentrated in vacuo
  3. customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 4:1)

Sources & evidence

ORD record
ord-896aee8267f0471894e194d1a54b51af
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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