Tetrahydrofuran → HCID 86702582, compound

HRID 1746815Notes

Reaction equation

HRID 1746815 reaction equation
[O:1]1CC[CH2:3][CH2:2]1.[CH3:6][Si:7]([CH3:37])([C:33]([CH3:36])([CH3:35])[CH3:34])[O:8][CH2:9][C@H:10]1[C@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13][C@H:12]([OH:22])[C@@H:11]1[CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.C1(C)C=CC=CC=1>C(OCC)(=O)C.CCCCCC.O.C(O)(=O)C>[C:2]([O:22][C@H:12]1[C@H:11]([CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])[C@@H:10]([CH2:9][O:8][Si:7]([CH3:6])([CH3:37])[C:33]([CH3:34])([CH3:36])[CH3:35])[C@H:14]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)[CH2:13]1)(=[O:1])[CH3:3]

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 13080739HCID 13080739, compoundHCID 66777355Diethylazodicarboxylate toluene

Product 1

HCID 86702582HCID 86702582, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

An anhydrous tetrahydrofuran (482 mL) solution of the compound 3 (79.6 g) and triphenylphosphine (57.6 g) was cooled to around −40° C. in a dry ice-methanol bath. To this solution was added acetic acid (12.6 mL), and a 40% diethyl azodicarboxylate/toluene solution (100 mL) was then added dropwise over 15 minutes. The mixture was stirred at room temperature for 4.5 hours, the reaction mixture was then poured into water (1600 mL), a mixed solution of hexane (550 mL) and ethyl acetate (550 mL) was added, and the mixture was stirred. The two layers were separated, and the organic layer was then washed with water (540 mL) and a saturated saline (540 mL), dried with anhydrous sodium sulfate, and concentrated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1) to obtain a titled compound (69.7 g) having the following physical property values.

Workup

  1. stirringthe mixture was stirred
  2. customThe two layers were separated
  3. washthe organic layer was then washed with water (540 mL)
  4. dry with materiala saturated saline (540 mL), dried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-891ca50e8aca404987e596f5c2729b41
Source dataset
uspto-grants-2015_10
Patent number
US09150537B2

Reaction notes

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