1,3-Dibromopropane → HCID 22854246, compound

HRID 22505Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][CH2:5][O:6][CH:7]1[CH2:12][CH2:11][C@H:10]2[C@H:13]3[C@H:22]([CH2:23][CH2:24][C@:8]12[CH3:9])[C:21]1[CH:20]=[CH:19][C:18]([OH:25])=[CH:17][C:16]=1[CH2:15][CH2:14]3.[Br:26][CH2:27][CH2:28][CH2:29]Br.[Cl-].[NH4+]>O1CCCC1.CN(C)C=O>[Br:26][CH2:27][CH2:28][CH2:29][O:25][C:18]1[CH:19]=[CH:20][C:21]2[C@@H:22]3[C@H:13]([C@H:10]4[C@@:8]([CH2:24][CH2:23]3)([CH3:9])[CH:7]([O:6][CH2:5][O:4][CH3:3])[CH2:12][CH2:11]4)[CH2:14][CH2:15][C:16]=2[CH:17]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of a 60 % sodium hydride (0.531 g) in tetrahydrofuran (100 ml) is cooled to 0° C., and 17-(methoxymethoxy)-estra-1,3,5(10)-trien-3-ol (3.5 g) is slowly added thereto. After addition of dimethylformamide (50 ml), the mixture is stirred at room temperature for 2 hours. To the resulting solution is added 1,3-dibromo-propane (2.68 g), and the mixture is stirred at room temperature overnight. The reaction mixture is poured into an aqueous ammonium chloride, followed by extraction with ethyl acetate. The solvent is removed under reduced pressure and the residue thus obtained is purified over column chromatography (n-hexane:ethyl acetate=2:1) to give 3-[(3-bromopropyl)oxy]- 17-(methoxymethoxy)-estra-1,3,5(10)-triene (3.0 g).

Workup

stirringthe mixture is stirred at room temperature overnight
extractionfollowed by extraction with ethyl acetate
customThe solvent is removed under reduced pressure
customthe residue thus obtained
customis purified over column chromatography (n-hexane:ethyl acetate=2:1)

Sources & evidence

ORD record: ord-2a0d345d4b8645418eee8e9458945cd1
Source dataset: uspto-grants-1995_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05428181

Reaction notes

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