Ethyl Acetate → HCID 13686452, compound

HRID 1981878Notes

Reaction equation

HRID 1981878 reaction equation
[C:1]([O:4][C@H:5]1[C@H:29]([F:30])[CH2:28][C@@:27]2([CH3:31])[CH:7]([C@H:8](O)[CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6]1)(=[O:3])[CH3:2].P(Cl)(Cl)(Cl)=O.C(OCC)(=O)C>N1C=CC=CC=1>[C:1]([O:4][C@H:5]1[C@H:29]([F:30])[CH2:28][C@@:27]2([CH3:31])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:26]2[CH2:25][CH2:24][C@@:23]2([CH3:32])[C@H:11]3[CH2:12][CH2:13][C@@H:14]2[C@H:15]([CH3:22])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:6]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 13686450HCID 13686450, compound

Product 1

HCID 13686452HCID 13686452, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of the acetate (7) (92 mg, 0.198 mmol) in pyridine (2 ml) was added dropwise phosphorusoxychloride (0.06 ml) at 0° and the mixture was stirred at room temperature for 2 hr. To the reaction mixture were added ice and ethyl acetate. The organic phase was washed with 2N-HCl, saturated NaHCO3 and brine, and dried over MgSO4. The residue obtained upon evaporation of the solvent was purified by column chromatography on silica gel (5 g). Elution with benzene-ethyl acetate (20:1) gave the olefine (8) (90 mg, 98%), mp 116°-119° (MeOH); δ0.68(3H s, 18H3), 0.87(6H, d, J=6 Hz, 26- and 27-H3), 0.93(3H, d, J=6 Hz, 21-H3), 1.06(3H, s, 19-H3), 2.08(3H, s, acetyl), 4.10-5.00(1 H, broad, 2β-H), 4.86(1H, m, 3α-H), and 5.42(1H, m, 6-H); m/z 386.3370(M+ -AcOH). (CH27H43F required M, 386.3347).

Workup

  1. washThe organic phase was washed with 2N-HCl, saturated NaHCO3 and brine
  2. dry with materialdried over MgSO4
  3. customThe residue obtained upon evaporation of the solvent
  4. customwas purified by column chromatography on silica gel (5 g)
  5. washElution with benzene-ethyl acetate (20:1)

Sources & evidence

ORD record
ord-2bb22aef9ecb488692ab822aa8542de1
Source dataset
uspto-grants-1986_06
Patent number
US04594192

Reaction notes

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