Acetic Acid → HCID 86741443, compound

HRID 543023Notes

Reaction equation

HRID 543023 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[O:6]=[C:7]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])CP(=O)([O-])[O-].[C:24]([O:27][C@H:28]1[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:43]([CH2:44][CH2:45][C@:29]12[CH3:30])[C:42]1[CH:41]=[CH:40][C:39]([O:46][C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[CH:38][C:37]=1[CH2:36][C@H:35]3CCC=O)(=[O:26])[CH3:25].C(O)(=O)C>CCCCCC.O1CCCC1>[C:24]([O:27][C@H:28]1[CH2:33][CH2:32][C@H:31]2[C@H:34]3[C@H:43]([CH2:44][CH2:45][C@:29]12[CH3:30])[C:42]1[CH:41]=[CH:40][C:39]([O:46][C:47](=[O:54])[C:48]2[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=2)=[CH:38][C:37]=1[CH2:36][C@H:35]3[CH2:4][CH2:3][CH:2]=[CH:1][C:7](=[O:6])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])(=[O:26])[CH3:25]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 20206901HCID 20206901, compoundHCID 86741444HCID 86741444, compoundHCID 178418339Butyllithium

Product 1

HCID 86741443HCID 86741443, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

n-Butyl-lithium (0.341 ml. of a 1.6 molar solution in hexane) was added to a stirred solution of 2-oxotridecylphosphonate (0.193 g.) in tetrahydrofuran (10 ml.) which was maintained at -70° C. and the mixture was stirred at that temperature for 40 minutes. A solution of 3-(17β-acetoxy-3-benzoyloxyoestra-1,3,5(10)-trien-7α-yl)propionaldehyde (Example 3; 0.2 g.) in tetrahydrofuran (10 ml.) was added and the mixture was allowed to warm up to laboratory temperature and was stirred at that temperature for 4.5 hours. Acetic acid was added until the mixture was acidic and the mixture was evaporated to dryness. Water (10 ml.) was added and the mixture was extracted three times with ethyl acetate (30 ml. each time). The combined extracts were washed with water, dried and evaporated to dryness and there was thus obtained as residual oil 1-(17β-acetoxy-3-benzoyloxyoestra-1,3,5(10)-trien-7α-yl)hexadec-3-en-5-one.

Workup

  1. temperatureto warm up to laboratory temperature
  2. stirringwas stirred at that temperature for 4.5 hours
  3. customthe mixture was evaporated to dryness
  4. additionWater (10 ml.) was added
  5. extractionthe mixture was extracted three times with ethyl acetate (30 ml
  6. washThe combined extracts were washed with water
  7. customdried
  8. customevaporated to dryness and there

Sources & evidence

ORD record
ord-580000efe708484dae508ec6c63cbafd
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

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