Chloroacetyl chloride → HCID 14981640, compound

HRID 2294782Notes

Reaction equation

HRID 2294782 reaction equation
[CH3:1][C@@:2]12[C@H:12]3[CH2:13][CH2:14][C@:15]4([CH3:21])[C@@H:19]([OH:20])[CH2:18][CH2:17][C@H:16]4[C@@H:11]3[CH2:10][CH2:9][C@H:8]1[CH2:7][C:5](=[O:6])[CH2:4][CH2:3]2.C(N(CC)CC)C.[Cl:29][CH2:30][C:31](Cl)=[O:32]>C(Cl)Cl.ClCl>[Cl:29][CH2:30][C:31]([O:20][C@H:19]1[CH2:18][CH2:17][C@H:16]2[C@H:11]3[C@H:12]([CH2:13][CH2:14][C@:15]12[CH3:21])[C@:2]1([CH3:1])[C@H:8]([CH2:7][C:5](=[O:6])[CH2:4][CH2:3]1)[CH2:9][CH2:10]3)=[O:32]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 10635Dihydrotestosterone

Product 1

HCID 14981640HCID 14981640, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 24526ChlorineSolvent

Conditions

Temperature
0 °C

Procedure

Dihydrotestosterone (2.6 mmol) was dissolved in anhydrous methylene chloride (3 mL) and triethylamine (2.6 mmol) under argon. The solution was stirred at 0° C. for 30 minutes at which time chloroacetyl chloride (3.75 mmol) dissolved in anhydrous methylene chloride (2 mL) was added. The resulting mixture was stirred for an additional 30 min at 0° C. and at room temperature for 4 hr. The solution was diluted with CH2 Cl2 (30 mL) and was washed with aqueous 0.05N hydrochloric acid (2×30 mL) and water (2×30 mL). The organic layer was dried over sodium sulfate and evaporated under vacuum to give crude product as a white solid. The product was purified by silica gel column chromatography (Davisil grade 633, 200-425 mesh, 60 Å) using CHCl3 as eluent. Yield, 0.38 g (41%); mp 135°-136° C. (lit. Ferguson et al., J. Chem. Soc., Perkin II, 3, 267-272 (1978)), 138° C.); 1H NMR δ0.78 (s, 3 H, CH3 -19), 0.98 (s, 3 H, CH3 -18), 0.78-2.49 (m, 22 H), 4.37 (d, 2 H, CH2Cl), 4.62 (t, 1 H, H-17); MS (EI) calcd m/z for C21H31O335Cl 366.1961, found, 366.1932; calcd. m/z for C21H31O337Cl 368.1932, found, 368.1911.

Workup

  1. additionwas added
  2. washwas washed with aqueous 0.05N hydrochloric acid (2×30 mL) and water (2×30 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated under vacuum
  5. customto give crude product as a white solid
  6. customThe product was purified by silica gel column chromatography (Davisil grade 633, 200-425 mesh, 60 Å)
  7. customYield

Sources & evidence

ORD record
ord-c3cd85ab8ef943a5b30f808fed0ffa59
Source dataset
uspto-grants-1997_11
Patent number
US05691307

Reaction notes

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