Methyl propiolate → HCID 53842172, compound

HRID 2199021Notes

Reaction equation

HRID 2199021 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[C:2]#[CH:3].[Br-].[Br-].[Br-].[Al+3].[C:11]([O:14][C@@H:15]1[C@@:33]2([CH3:34])[C:19](=[CH:20][CH2:21][C@@H:22]3[C@@H:32]2[CH2:31][CH2:30][C@@:29]2([CH3:35])[C@H:23]3[CH2:24][CH2:25]/[C:26]/2=[CH:27]/[CH3:28])[CH2:18][C@@H:17]([O:36][C:37](=[O:39])[CH3:38])[CH2:16]1)(=[O:13])[CH3:12]>C(Cl)Cl>[CH3:6][O:5][C:1](=[O:4])[CH:2]=[CH:3][C@H:27]([C:26]1[C@:29]2([CH3:35])[C@H:23]([C@H:22]3[C@H:32]([CH2:31][CH2:30]2)[C@:33]2([CH3:34])[C:19]([CH2:18][C@@H:17]([O:36][C:37](=[O:39])[CH3:38])[CH2:16][C@@H:15]2[O:14][C:11](=[O:13])[CH3:12])=[CH:20][CH2:21]3)[CH2:24][CH:25]=1)[CH3:28]

Participants

5

Reactant 3

HCID 13536Methyl propiolateHCID 166749BromhydrolHCID 12851145HCID 12851145, compound

Product 1

HCID 53842172HCID 53842172, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.13 ml (1.5 mmol) of methyl propiolate in 10 ml of dry methylene chloride (over 4 A molecular sieves) under a nitrogen atmosphere was added 0.954 g (3.5 mmol) of aluminum tribromide. Immediately thereafter was added 398 mg (1 mmol) of Z-pregna-5,17(20)-diene-1α,3β-diol diacetate dissolved in 10 ml dry methylene chloride. The orange-colored solution was stirred for 15 min. A 2-ml sample was quenched with 5 ml of 10% aqueous potassium sodium tartrate salts. Analysis of the organic phase showed 20% of 1α,3β-diacetyloxychola-5,16,22-trien-24-oic acid methyl ester had formed (GC analysis).

Workup

  1. customA 2-ml sample was quenched with 5 ml of 10% aqueous potassium sodium tartrate salts
  2. customhad formed (GC analysis)

Sources & evidence

ORD record
ord-d0761250626b4bbbbff0456177dd6071
Source dataset
uspto-grants-1982_11
Patent number
US04360470

Reaction notes

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