Isopropanol → HCID 22004770, compound

HRID 324587Notes

Reaction equation

[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[CH:19]([C:20]([O:22][CH3:23])=[O:21])[C:18](=[O:24])[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:16]=4)[O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:30]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:35]=CC=C[CH:31]=1.C(O)(C)C.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]3[C:19]([C:20]([O:22][CH3:23])=[O:21])=[C:18]([O:24][CH:30]([CH3:35])[CH3:31])[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:16]=4)[O:11]3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

Conditions

Temperature: -10 °C

Procedure

The compound (VII-3) was converted to methyl 2-(benzo[1,3]dioxol-5-yl)-6-butoxy-4-oxo-chroman-3-carboxylate (IV-3) by a similar method as Step 5 of Reference Example 2. Compound (V-3) (250 mg, 0.628 mmol), triphenylphosphine (247 mg, 0.943 mmol) and isopropanol (57 mg, 0.943 mmol) were dissolved in 7 ml of THF and cooled to −10° C. A solution of diethylazodicarboxylate (164 mg, 0.943 mmol) in THF (2 ml) was added dropwise and stirred for 2 h at the same temperature. After the solvent was removed under reduced pressure, the residue was purified by 10 g of silica gel chromatography (ethyl acetate/hexane=1:4) to give the compound (Ia-11) (220 mg, 80%) as a yellow oil.

Workup

customAfter the solvent was removed under reduced pressure
customthe residue was purified by 10 g of silica gel chromatography (ethyl acetate/hexane=1:4)
customto give the compound (Ia-11) (220 mg, 80%) as a yellow oil

Sources & evidence

ORD record: ord-98f5c22e67ca4f33b0fbead0fd405053
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06218427B1

Reaction notes

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