Water → HCID 11270256, compound

HRID 2118216Notes

Reaction equation

HRID 2118216 reaction equation
O[C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:18]2[CH:23]=[CH:22][C:21](/[CH:24]=[CH:25]/[C:26]([O:28][Si](C(C)(C)C)(C)C)=[O:27])=[CH:20][CH:19]=2)=[C:9](\[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)/[CH2:10][CH3:11])=[CH:4][CH:3]=1.CCN(CC)CC.[C:43](Cl)(=[O:46])[CH2:44][CH3:45].[OH2:48]>C(Cl)Cl.C1COCC1>[C:12]1(/[C:9](/[CH2:10][CH3:11])=[C:8](/[C:18]2[CH:19]=[CH:20][C:21](/[CH:24]=[CH:25]/[C:26]([OH:28])=[O:27])=[CH:22][CH:23]=2)\[C:5]2[CH:4]=[CH:3][C:2]([O:48][C:43](=[O:46])[CH2:44][CH3:45])=[CH:7][CH:6]=2)[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 59816254HCID 59816254, compound

Product 1

HCID 11270256HCID 11270256, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 30 (0.10 g, 0.20 mmol) in CH2Cl2 (5 mL) was added Et3N (0.072 mL, 0.052 g, 0.51 mmol) and propionyl chloride (0.021 mL, 0.021 g, 0.22 mmol). The mixture was stirred at ambient temperature for 1 h, washed with H2O (2×), dried (Na2SO4), concentrated, and dried in vacuo to give an off-white foam. This residue was dissolved in THF (3 mL) and H2O (0.6 mL) and the mixture was stirred at ambient temperature for 5 h. Solvent was evaporated and the residue triturated with hexanes/Et2O (5:1) to provide 7 (0.064 g, 73%) as an off-white solid, mp 155-157° C. 1HNMR (DMSO-d6): δ 0.86 (t, J=7.4 Hz, 3H), 1.05 (t, J=7.4 Hz, 3H), 2.4 (q, J=7.4 Hz, 2H), 2.49 (q, J=7.4 Hz, 2H), 6.51 (d, J=16 Hz, 1H), 6.79 (d, J=8.6 Hz, 2H), 6.85 (d, J=8.6 Hz, 2H), 7.10-7.22 (m, 5H), 7.25 (d, J=8.1 Hz, 2H), 7.59 (d, J=16 Hz, 1H), 7.7 (d, J=8.1 Hz, 2H), 12.33 (br s, 1H); Anal. calculated for C28H26O4.0.25H2O: C, 78.03; H, 6.20; Found: C, 78.02; H, 6.13.

Workup

  1. washwashed with H2O (2×)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customdried in vacuo
  5. customto give an off-white foam
  6. customSolvent was evaporated
  7. customthe residue triturated with hexanes/Et2O (5:1)

Sources & evidence

ORD record
ord-fe4f5682b3104481b433c6c1b7dca72b
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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