Phthalimide → Cis-1-Phthalimido-4-Tetrahydropyranyloxy-2-Butene

HRID 36580Notes

Reaction equation

HRID 36580 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:19][CH2:20]/[CH:21]=[CH:22]\[CH2:23]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:44]1(=[O:54])[NH:48][C:47](=[O:49])[C:46]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:45]12>O1CCCC1>[C:44]1(=[O:54])[N:48]([CH2:23]/[CH:22]=[CH:21]\[CH2:20][O:19][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)[C:47](=[O:49])[C:46]2=[CH:50][CH:51]=[CH:52][CH:53]=[C:45]12

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10975949(Z)-4-(Tetrahydro-2H-pyran-2-yl-oxy)but-2-en-1-ol

Product 1

HCID 14722756Cis-1-Phthalimido-4-Tetrahydropyranyloxy-2-ButeneYield 64%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere diethylazodicarboxylate (1.6 ml, 10 mmol) was added to a cooled (0° C.) solution of cis-4-tetrahydropyranyloxy-2-butene-1-ol (1.7 g, 10 mmol), triphenyl phosphine (2.2 g, 10 mmol) and phthalimide (1.47 g, 10 mmol) in anhydrous tetrahydrofuran (50 ml). When the addition was completed (5 min) the reaction mixture was allowed to warm at room temperature and was stirred 12 h. Then the mixture was concentrated in vacuo, diluted with ethyl acetate (200 ml) and washed with brine (150 ml). After usual work-up (the aqueous phase was extracted three times with 100 ml portions of ethyl acetate), the organic phase was dried over magnesium sulfate, filtered and concentrated in vacuo) the product was purified by flash chromatography on silica gel (ethyl acetate:hexane; 2:8) to give 1.9 g of the title compound (64%).

Workup

  1. additionWhen the addition
  2. custom(5 min)
  3. concentrationThen the mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate (200 ml)
  5. washwashed with brine (150 ml)
  6. extractionAfter usual work-up (the aqueous phase was extracted three times with 100 ml portions of ethyl acetate), the organic phase
  7. dry with materialwas dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo) the product
  10. customwas purified by flash chromatography on silica gel (ethyl acetate:hexane; 2:8)

Sources & evidence

ORD record
ord-4f5ab32b7a6443958190e1d5418a8f94
Source dataset
uspto-grants-1995_05
Patent number
US05416076

Reaction notes

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