1,3-Propanediol → HCID 131720726, compound

HRID 964827Notes

Reaction equation

HRID 964827 reaction equation
[CH3:1]COC(/N=N/C(OCC)=O)=O.C([C:17]1[C:18]([O:26][SiH:27]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[C:19]([CH:23]=[CH:24][CH:25]=1)[C:20]([OH:22])=[O:21])(C)(C)C.C1(P([C:53]2[CH:58]=[CH:57]C=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:59](O)[CH2:60][CH2:61]O>C1COCC1>[O:26]([C:18]1[CH:17]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([O:22][CH2:53][CH2:58][CH3:57])=[O:21])[Si:27]([C:60]([CH3:61])([CH3:1])[CH3:59])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 4

HCID 104421,3-PropanediolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 178440887HCID 178440887, compound

Product 1

HCID 131720726HCID 131720726, compoundYield 73.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

DEAD (0.14 g, 0.00079 mol) was added to a solution of acid 23 (0.3 g, 0.00079 mol) dissolved in anhydrous THF (10 mL). A mixture of triphenylphosphine (0.21 g, 0.0008 mol) and 1,3-propanediol (0.091 g, 0.0011 mol) in THF (3 mL) was injected slowly to the above solution and reaction mixture stirred at room temperature for 24 hours. The solution was quenched with H2O (12 mL) and extracted with ethyl acetate (2×15 mL). The organic layer was dried over anhydrous Na2 SO4 and concentrated under reduced pressure. Purification by preparative TLC (ethylacetate/hexane, 70:30) gave the pure ester (24) (0.25 g, 0.00058 mol, 73%). 1H NMR (CDCl3) δ 1.11 (S, 9H), 1.88-1.96 (m, 2H), 2.49 (bs, 1H), 3.67 (t, 2H, J=6 Hz), 4.38 (t, 2H, J=6Hz), 6.86-7.72 (m, 14H). M.S. Exact mass: calculated 434.4126, found M+1, 435.

Workup

  1. customwas injected slowly to the above solution and reaction mixture
  2. customThe solution was quenched with H2O (12 mL)
  3. extractionextracted with ethyl acetate (2×15 mL)
  4. customThe organic layer was dried over anhydrous Na2 SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification by preparative TLC (ethylacetate/hexane, 70:30)

Sources & evidence

ORD record
ord-16fbf3615f8b48fa936b80e3b13ac5b8
Source dataset
uspto-grants-1998_06
Patent number
US05770743

Reaction notes

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