HCID 20206882, compound → HCID 70446889, compound

HRID 543012Notes

Reaction equation

HRID 543012 reaction equation
[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[Br-].[CH2:7]([N:11]([CH3:42])[C:12]([CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:13])[CH2:8][CH2:9][CH3:10].C([O:50][C:51]1[CH:68]=[CH:67][C:66]2[C:65]3[CH2:64][CH2:63][C@@:61]4([CH3:62])[C:57](=[CH:58][CH2:59][C@@H:60]4[OH:69])[C:56]=3C(C=O)=C[C:53]=2[CH:52]=1)C1C=CC=CC=1>CCCCCC.CS(C)=O.O1CCCC1>[CH2:1]([O:50][C:51]1[CH:68]=[CH:67][C:66]2[C:65]3[CH2:64][CH2:63][C@@:61]4([CH3:62])[C:57](=[CH:58][CH2:59][C@@H:60]4[OH:69])[C:56]=3[C:14]([CH:15]=[CH:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:12]([N:11]([CH2:7][CH2:8][CH2:9][CH3:10])[CH3:42])=[O:13])=[CH:12][C:53]=2[CH:52]=1)[C:2]1[CH:9]=[CH:8][CH:7]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 20206882HCID 20206882, compoundHCID 86741437HCID 86741437, compoundHCID 178418339Butyllithium

Product 1

HCID 70446889HCID 70446889, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

Butyl-lithium (0.8 ml. of a 1.6 molar solution in hexane) was added dropwise to a stirred solution of [9-(N-n-butyl-N-methylcarbamoyl)nonyl]triphenylphosphonium bromide (1.2 g.) in a mixture of dimethyl sulphoxide (2 ml.) and tetrahydrofuran (18 ml.), a solution of 3-benzyloxy-17β-hydroxyoestra-1,3,5(10),6,8(9),14(15)-hexaene-7-carboxaldehyde (0.05 g.) in tetrahydrofuran (2 ml.) was then added and the mixture was stirred at laboratory temperature for 1 hour and then evaporated to dryness under reduced pressure. Water (15 ml.) was added and the mixture was extracted three times with ethyl acetate (10 ml. each time) and the combined extracts were washed with water, dried and evaporated to dryness. The residue was purified by chromatography on a silica gel column using a 3:1 v/v mixture of petroleum ether (b.p. 60°-80° C.) and acetone as eluant. There was thus obtained as an oil 11-(3-benzyloxy-17β-hydroxyoestra-1,3,5(10),6,8(9),14(15)-hexaen-7-yl)-N-n-butyl-N-methylundec-10-enamide.

Workup

  1. customevaporated to dryness under reduced pressure
  2. additionWater (15 ml.) was added
  3. extractionthe mixture was extracted three times with ethyl acetate (10 ml
  4. washeach time) and the combined extracts were washed with water
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified by chromatography on a silica gel column
  8. additiona 3:1 v/v mixture of petroleum ether (b.p. 60°-80° C.) and acetone as eluant

Sources & evidence

ORD record
ord-49c26636368e409c88ca23e520379b38
Source dataset
uspto-grants-1987_04
Patent number
US04659516

Reaction notes

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