Dimethyl Sulfoxide → HCID 69105455, compound

HRID 2219065Notes

Reaction equation

HRID 2219065 reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH3:6].[NH2-].[Na+].[OH:28][C:29]1[CH:46]=[CH:45][C:44]2[C@:43]3([CH:47]=O)[C@H:34]([C@H:35]4[C@@:39]([CH2:41][CH2:42]3)([CH3:40])[CH2:38][C@H:37]([OH:49])[CH2:36]4)[CH2:33][CH2:32][C:31]=2[CH:30]=1.CS(C)=O.O>C(OCC)(=O)C>[CH:47]([C@:43]12[CH2:42][CH2:41][C@@:39]3([CH3:40])[C@@H:35]([CH2:36][C@@H:37]([OH:49])[CH2:38]3)[C@@H:34]1[CH2:33][CH2:32][C:31]1[CH:30]=[C:29]([OH:28])[CH:46]=[CH:45][C:44]2=1)=[CH:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 12095978HCID 12095978, compoundHCID 86620370HCID 86620370, compound

Product 1

HCID 69105455HCID 69105455, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

8.68 g (20 mmol) of pentyltriphenyl-phosphonium bromide+sodium amide (1 g contains 2.3 mmol of pentyltriphenyl-phosphonium bromide), 0.2 g (0.67 mmol) of 3,16α-dihydroxy-estra-1,3,5(10)-triene-9-carbaldehyde and 30 ml DMSO are introduced into a reaction flask that was rendered inert. The reaction mixture is treated for about 2 hours in an ultrasound bath at 60° C. After the reaction is completed, water is added to the reaction solution. The crude product is isolated by extraction with ethyl acetate, washing of the organic phase with water and concentration by evaporation until a dry state is reached.

Workup

  1. additionThe reaction mixture is treated for about 2 hours in an ultrasound bath at 60° C

Sources & evidence

ORD record
ord-e380c47c750743abb1eceeeca8532f8e
Source dataset
uspto-grants-2008_08
Patent number
US07414043B2

Reaction notes

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