Diisopropylamine → HCID 14350160, compound

HRID 414287Notes

Reaction equation

HRID 414287 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]([OH:17])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[OH:18][CH:19]([C:27]#[CH:28])[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24].C(NC(C)C)(C)C>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:17][CH:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:28]#[C:27][CH:19]([OH:18])[CH2:20][CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 14444695Methyl 5-hydroxyhept-6-ynoateHCID 14677849HCID 14677849, compound

Product 1

HCID 14350160HCID 14350160, compoundYield 129.2%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Into a heavy walled pyrex test tube was added 130 mg (0.43 mmol) of 1-(0-bromophenyl)-1-nonanol, 67 mg (0.43 mmol) of methyl 5-hydroxy-6-heptynoate prepared according to the procedure of Nicolaou et al., J.A.C.S., 106, 2748 (1984), 25 mg (0.02 mmol, 5 mole%) of Pd(PPh3)4, and 4 ml (93.0 mg) of diisopropylamine. The reaction was run and worked up according to the procedure of Example 11 to yield 208 mg of a yellow-brown oil. The oil was chromatographed on a silica gel column which was eluted with 70% diethyl ether/hexane to produce the titled product as a yellow oil.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-c379ae8141b64759aafad911931137eb
Source dataset
uspto-grants-1988_12
Patent number
US04791133

Reaction notes

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