TBAF tetrahydrofuran → HCID 56622945, compound

HRID 2288078Notes

Reaction equation

[CH3:1][C:2]([O:10][C:11]([C:13]12[C:24]3([CH:26]=[O:27])[CH2:25][CH:16]([C:17]1([CH2:29][O:30][C:31]14[CH:43]([O:44][Si](C(C)(C)C)(C)C)[CH:37]5[CH:38]([O:39][CH2:40][CH2:41][CH3:42])[CH:33]([CH:34]([O:36]5)[O:35]1)[O:32]4)[CH2:18][CH:19]1[CH:23]3[CH2:22][CH2:21][CH:20]1[CH3:28])[CH:15]=[C:14]2[CH:52]([CH3:54])[CH3:53])=[O:12])([CH3:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>>[CH3:1][C:2]([O:10][C:11]([C:13]12[C:24]3([CH:26]=[O:27])[CH2:25][CH:16]([C:17]1([CH2:29][O:30][C:31]14[CH:43]([OH:44])[CH:37]5[CH:38]([O:39][CH2:40][CH2:41][CH3:42])[CH:33]([CH:34]([O:36]5)[O:35]1)[O:32]4)[CH2:18][CH:19]1[CH:23]3[CH2:22][CH2:21][CH:20]1[CH3:28])[CH:15]=[C:14]2[CH:52]([CH3:53])[CH3:54])=[O:12])([CH3:9])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 11078149TBAF tetrahydrofuran

HCID 56623178HCID 56623178, compound

Product 1

HCID 56622945HCID 56622945, compoundYield 89.6%

Procedure

21 mg of compound (30) was mixed with 53.2 μl of 1M tetrabutylammonium fluoride-tetrahydrofuran solution, and the reaction was conducted at room temperature under stirring for 2 hours. The reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm) and eluted with n-hexane-ethyl acetate (2:1). The fraction containing the desired product was concentrated to dryness to give 16 mg of compound (31).

Workup

customwas conducted at room temperature
additionThe reaction solution was charged onto a silica gel column (Kieselgel 60, Merck, 1.0φ×30 cm)
washeluted with n-hexane-ethyl acetate (2:1)
additionThe fraction containing the desired product
concentrationwas concentrated to dryness

Sources & evidence

ORD record: ord-920e5b232d4544198f03b0e60f0ba86d
Source dataset: uspto-grants-2000_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06087390

Reaction notes

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