Tetrahydrofuran → HCID 21265710, compound

HRID 566515Notes

Reaction equation

HRID 566515 reaction equation
[F:1][C:2]([F:46])([P:42]([OH:45])(O)=[O:43])[C:3]1[CH:41]=[CH:40][C:6]([CH2:7][C:8]([C:32]2[CH:37]=[CH:36][C:35](SC)=[CH:34][CH:33]=2)([C:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27](F)[CH:26]=2)=[O:24])[CH2:9][C:10]2[CH:15]=[CH:14][C:13](OP(C(F)F)(=O)O)=[CH:12][CH:11]=2)=[CH:5][CH:4]=1.[CH2:47]1OCCOCCOCCOCCOCCOC1.[CH3:65][C:66]([CH3:69])([O-:68])[CH3:67].[K+].BrCC1C=CC([C:79]([F:88])([F:87])[C:80]([O:82]C(C)(C)C)=[O:81])=CC=1.[CH2:89]1[CH2:93]OC[CH2:90]1>[N+](CCCC)(CCCC)(CCCC)CCCC.[I-]>[C:66]([O:68][P:42]([C:2]([F:1])([F:46])[C:3]1[CH:41]=[CH:40][C:6]([CH2:7][C:8]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)([C:23](=[O:24])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([C:79]([F:88])([F:87])[C:80]([OH:82])=[O:81])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)([O:45][C:89]([CH3:90])([CH3:93])[CH3:47])=[O:43])([CH3:69])([CH3:67])[CH3:65]

Participants

7

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 2855718-Crown-6HCID 14888669HCID 14888669, compoundHCID 23665647Potassium tert-butoxideHCID 88067715HCID 88067715, compound

Product 1

HCID 21265710HCID 21265710, compound

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Procedure

To the compound of Example 33 (0.100 g, 0.189 mmol) in THF (0.90 mL) were added nBu4NI (catalytic) and a trace of 18-crown-6. To this mixture at −78° C. was added potassium tert-butoxide (1M in THF, 0.208 mL) after a period of 10 min at −78° C., a THF solution (0.30 mL) of tert-butyl 2-[4-(bromomethyl)phenyl]-2,2-difluoroacetate](0.066 g, 0.206 mmol) was added. After a period of 2 h, at 0° C., the reaction mixture was quenched as described for Example 31 Step 1.

Workup

  1. customat 0° C., the reaction mixture was quenched

Sources & evidence

ORD record
ord-4d010512c9ed495d9b6d46dbf2a5252a
Source dataset
uspto-grants-2001_01
Patent number
US06174874B1

Reaction notes

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