Triphenylphosphine → HCID 87106866, compound

HRID 922301Notes

Reaction equation

HRID 922301 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[CH3:21][O:22]/[N:23]=[C:24](/[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)\[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33]O)=[CH:29][CH:28]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(OCC)(=O)C>[CH3:21][O:22]/[N:23]=[C:24](/[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)\[CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([CH2:33][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH:8]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=2)=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 57835819HCID 57835819, compoundHCID 86695770(4-{[(2E)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol

Product 1

HCID 87106866HCID 87106866, compoundYield 52.17%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 100 mL of two neck RB flask was charged ethyl 3-(4-hydroxyphenyl)-3-phenylpropanoate (0.6 g, 2.2 mmol) and (4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}phenyl)methanol (0.6 g, 2.2 mmol) in 20 mL of THF. To this added triphenyl phosphine (0.755 g, 2.88 mmol) at 0° C. and added DIAD (0.59 g, 2.88 mmol) portion wise over a period of 15 min at 0° C. After 12 h of stirring at RT, the mixture was diluted with Ethyl acetate, washed with water and brine solution successively. Organic phase was dried over anhydrous Na2SO4 and concentrated to afford yellow oil as product (0.6 g, yield: 52.17%); 1H NMR (300 MHz, DMSO-d6): δ 7.57-7.60 (m, 2H), 7.06-7.31 (m, 12H), 6.84-6.86 (m, 4H), 5.12 (s, 2H), 4.84 (s, 2H), 4.39-4.45 (t, 1H), 3.86-4.01 (m, 5H), 2.92-2.95 (d, 2H), 1.00-1.05 (t, 3H).

Workup

  1. washwashed with water and brine solution successively
  2. dry with materialOrganic phase was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto afford yellow oil as product (0.6 g, yield: 52.17%)

Sources & evidence

ORD record
ord-7ca83e88c3a448a696846781bcaf03f5
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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