Trimethylphosphine → HCID 58668698, compound

HRID 2356981Notes

Reaction equation

HRID 2356981 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:8]([C:11]2[CH:20]=[C:19]3[C:14]([CH:15](O)[CH2:16][CH2:17][O:18]3)=[CH:13][CH:12]=2)(=[O:10])=[O:9])[CH:5]=[CH:6][CH:7]=1.[CH:22]([C:33]([O:35][CH2:36][CH3:37])=[O:34])([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:23]([O:25][CH2:26][CH3:27])=[O:24].P(C)(C)C.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C1(C)C=CC=CC=1>[CH2:31]([O:30][C:28](=[O:29])[C:22]([C:33]([O:35][CH2:36][CH3:37])=[O:34])([CH:15]1[C:14]2[C:19](=[CH:20][C:11]([S:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=3)(=[O:9])=[O:10])=[CH:12][CH:13]=2)[O:18][CH2:17][CH2:16]1)[C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH3:32]

Participants

7

Reactant 4

HCID 68983TrimethylphosphineHCID 80471Triethyl methanetricarboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 58668696HCID 58668696, compound

Product 1

HCID 58668698HCID 58668698, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 7-(3-Fluorobenzene-sulfonyl)-chroman-4-ol (3.0 g, 9.7 mmol) in THF (40 ml) and toluene (40 ml) was added HC(COOEt)3 (4.5 g, 19.5 mmol) and then PMe3 (19.5 ml of 1.0M THF solution). The mixture was cooled to −78° C. DIAD (4.0 g, 19.5 mmol) was added dropwise. The mixture was stirred at −78° C. for 1 hour and then at RT for overnight. The next day the TLC showed that the reaction was complete. The solvent was removed and the residue was partitioned between EtOAc and H2O. The EtOAc layer was washed with brine, dried with MgSO4, concentrated and purified with flash column to give 2-Ethoxycarbonyl-2-[7-(3-fluoro-benzenesulfonyl)-chroman-4-yl]-malonicacid diethyl ester: 5.0 g, clear oil. MS: 545 (M+Na)+.

Workup

  1. waitat RT for overnight
  2. customThe solvent was removed
  3. customthe residue was partitioned between EtOAc and H2O
  4. washThe EtOAc layer was washed with brine
  5. dry with materialdried with MgSO4
  6. concentrationconcentrated
  7. custompurified with flash column

Sources & evidence

ORD record
ord-1c98dc4b21584485a00bb04f03d15bd8
Source dataset
uspto-grants-2010_07
Patent number
US07759389B2

Reaction notes

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