Ethyl chloroformate → HCID 21548938, compound

HRID 1605052Notes

Reaction equation

HRID 1605052 reaction equation
[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:15]([CH3:19])[C:16](O)=[O:17].ClC(OCC)=O.[BH4-].[Na+].C(=O)([O-])OCC.C1C2CC3C(=CC=CC=3)OC=2C=CC=1C(C(=O)OC(=O)OCC)C>O.C1COCC1.C(N(CC)CC)C>[CH:1]1[C:14]2[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][C:2]=1[CH:15]([CH3:19])[CH2:16][OH:17]

Participants

9

Reactant 5

HCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 12274162HCID 12274162, compoundHCID 21226545CID 21226545HCID 21548921HCID 21548921, compound

Product 1

HCID 21548938HCID 21548938, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

2.54 g. of 2-(2-xanthenyl)-propionic acid is dissolved in 20 ml. of absolute THF and combined with 1 ml. of triethylamine. At -10°, a solution of 0.6 ml. of ethyl chloroformate in 4 ml. of THF is added dropwise within 15 minutes, the mixture is stirred for 30 minutes at -10° and then 0.5 g. of NaBH4 is introduced into the solution which contains the mixed anhydride of monoethyl carbonate and the aforementioned acid, 2-(2-xanthenyl)-4,6-dioxaoctane-3,5-dione. Thereafter, the mixture is stirred for 90 minutes at 25°, 10 ml. of water is added, the mixture extracted with ether, evaporated, and the thus-obtained residue refluxed for 30 minutes with a solution of 0.25 g. of KOH in 10 ml. of ethanol. After the ethanol has been distilled off, the mixture has been worked up as usual, and the product chromatographed on Al2O3, 2-(2-xanthenyl)-propanol is obtained, m.p. 86°-89°.

Workup

  1. customAt -10°
  2. stirringThereafter, the mixture is stirred for 90 minutes at 25°
  3. extractionthe mixture extracted with ether
  4. customevaporated
  5. temperaturethe thus-obtained residue refluxed for 30 minutes with a solution of 0.25 g
  6. distillationAfter the ethanol has been distilled off
  7. customchromatographed on Al2O3

Sources & evidence

ORD record
ord-ebeb995e40414c139fa75f4ca589df84
Source dataset
uspto-grants-1976_04
Patent number
US03948949

Reaction notes

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