Sodium Chloride → HCID 131710775, compound

HRID 2398201Notes

Reaction equation

HRID 2398201 reaction equation
[H-].[Na+].[Br-].[C:4]([CH2:7][CH2:8][CH2:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([OH:6])=[O:5].[CH3:30][C:31]1([CH3:59])[CH2:36][O:35][C:34]2([CH2:40][CH2:39][CH:38](/[CH:41]=[CH:42]/[CH:43]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[O:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][O:46]3)[CH:37]2[CH2:56][CH:57]=O)[O:33][CH2:32]1.S([O-])(O)(=O)=O.[Na+].[Cl-].[Na+]>CS(C)=O.C(OCC)C>[CH3:59][C:31]1([CH3:30])[CH2:36][O:35][C:34]2([CH2:40][CH2:39][CH:38](/[CH:41]=[CH:42]/[CH:43]([CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])[O:44][CH:45]3[CH2:50][CH2:49][CH2:48][CH2:47][O:46]3)[CH:37]2[CH2:56]/[CH:57]=[CH:10]\[CH2:9][CH2:8][CH2:7][C:4]([OH:6])=[O:5])[O:33][CH2:32]1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 161236(4-Carboxybutyl)triphenylphosphonium bromideHCID 516919Sodium BisulfateHCID 21434829HCID 21434829, compound

Product 1

HCID 131710775HCID 131710775, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 3283Diethyl EtherSolvent

Procedure

640 mg of 80 % sodium hydride and 6 ml of dimethyl sulfoxide were heated for 1 hour to 65° C and, after cooling to room temperature, 4.7 g of 4-carboxybutyl-triphenylphosphonium-bromide in 8 ml of dimethylsulfoxide under argon were added and stirred for 20 minutes. To the red solution, 1.7 g of [3,3-dimethyl-8-[3-pentyl-3-tetra-hydropyranyloxy-trans-1-propenyl]-1,5-dioxaspiro-[5,4]-dec-7-yl]-acetaldehyde in 4 ml of dimethylsulfoxide were added dropwise and stirred for 15 hours at room temperature. 5% sodium hydrogen sulfate solution was added to that solution until pH 1 was reached, 50 ml of saturated sodium chloride solution were added and the mixture was esterified 3 times with 200 ml of diethyl ether, the combined organic phases were washed with water, dried and condensed.

Workup

  1. stirringstirred for 15 hours at room temperature
  2. washthe combined organic phases were washed with water
  3. customdried
  4. customcondensed

Sources & evidence

ORD record
ord-c15ba3bc1d744c20ada1d18da5cc750f
Source dataset
uspto-grants-1977_05
Patent number
US04024181

Reaction notes

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