Isopropanol → HCID 66859480, compound

HRID 1661126Notes

Reaction equation

HRID 1661126 reaction equation
C([C:4]1([OH:33])[CH2:9][CH2:8][C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]12[CH3:6])[C:18]1[CH:17]=[C:16]([O:22][CH2:23][CH3:24])[C:15]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[CH:14][C:13]=1[CH2:12][CH2:11]3)C=C.C1OCCOCCOCCOCCOCCOC1.[CH3:52][CH:53](O)[CH3:54].[NH4+].[Cl-]>C1COCC1>[CH2:54]([C@@H:8]1[C@H:7]2[C@H:10]3[C@H:19]([CH2:20][CH2:21][C@:5]2([CH3:6])[C:4](=[O:33])[CH2:9]1)[C:18]1[CH:17]=[C:16]([O:22][CH2:23][CH3:24])[C:15]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)=[CH:14][C:13]=1[CH2:12][CH2:11]3)[CH:53]=[CH2:52]

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 2855718-Crown-6HCID 66859063HCID 66859063, compound

Product 1

HCID 66859480HCID 66859480, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

KH 30% in oil (89.98 mmol) was suspended in THF (50 ml), under N2 atmosphere. 17-Allyl-3-(benzyloxy)-2-ethoxy-estra-1,3,5(10)-trien-17-ol (7.7 g, 17.30 mmol) and 18-Crown-6 (88.25 mmol) were dissolved in THF (200 ml) and added dropwise in 40 min. The mixture was stirred for 3 h at RT. The mixture was carefully poured into IPA via canula. The mixture was poured into aq. sat. NH4Cl (1 l). The water layer was extracted with EtOAc (3×250 ml). The combined organic layers were washed with brine (1×500 ml), dried over Na2SO4 and concentrated in vacuo. Purification via filtration over Silica (eluens heptan to 40% DCM in heptan) provided 4.2 g (9.51 mmol, 55%) of (XXX-(C2-D)-2c).

Workup

  1. additionadded dropwise in 40 min
  2. extractionThe water layer was extracted with EtOAc (3×250 ml)
  3. washThe combined organic layers were washed with brine (1×500 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customPurification
  7. filtrationvia filtration over Silica (eluens heptan to 40% DCM in heptan)
  8. customprovided 4.2 g (9.51 mmol, 55%) of (XXX-(C2-D)-2c)

Sources & evidence

ORD record
ord-8aa2053b2feb48ae8b60f620e595977a
Source dataset
uspto-grants-2011_10
Patent number
US08030298B2

Reaction notes

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